Questions tagged [ethers]
This tag is for questions relating to ethers: compounds containing an $\ce{R-O-R}$ fragment. It can be applied to the synthesis of, synthesis from and properties of ethers. If one of the $\ce{R}$ groups noted above is a carbonyl group, use *esters* instead. If both are, *carbonyl-compounds* is appropriate. This tag should not be used if the ether functionality is minor compared to others, or if it does not take part in the reaction in question.
85
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How to name ether with ketone and carboxyl groups?
Carboxylic acid is the main functional group due to higher priority, but since it's an ether, what's the proper way to name the following compound?
My attempt: 2-(1-methyl oxo propyl ether) ethanoic ...
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5
votes
1
answer
228
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Does boric acid really rearrange phenols?
This reaction was on prepchem.com and I want to know whether it could work. Most of their reactions are well sourced but this is rather scant (and can't find the patent referenced).
It is possible ...
- 237
2
votes
1
answer
164
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1H-NMR: How does the oxygen in ethers act as a spin coupling barrier while the oxygen in hydroxy groups doesn't?
It is possible to observe coupling between a hydroxyl proton and other protons. Why does the oxygen atom in ethers prevent any further coupling and act as a sort of barrier between spin systems? Or is ...
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0
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Ion from unsaturated ether
As far as I am concerned, from unsaturated primary/secondary amines (enamines) we obtain imines, like we do obtain carbonyls from enols, by tautomerism. For tertiary enamines, we have a corresponding ...
-2
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1
answer
45
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Favoured reaction product in acid catalysed addition of methanol to alkene [closed]
I would like to add methanol to an alkene RCH=CH2, catalysed by conc. sulphuric acid. I would like to know which of these endproducts will be preferentially produced:
RCH(OMe)-CH3
RCH2-CH2OMe
Many ...
- 15
2
votes
1
answer
223
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How does 81-crown-27 complexes itself with alkali metal with its size?
The biggest crown ether experimentally confirmed is 81-crown-27 1
How can this molecule form complexes when the distance between the 27 oxygen atoms which complexes with the cation inside seems ...
- 204
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0
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33
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Bond angle in ethers due to lone pair and bond pair repulsions
When I was learning VSEPR theory, we were taught that lone pair–lone pair repulsions are maximum followed by lone pair–bond pair and then bond pair–bond pair repulsions.
The bond angle in dimethyl ...
- 15
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How do mechanisms of acidic cleavage of ethers differ for anhydrous, concentrated, and aqueous HI?
I have seen the usage of anhydrous, concentrated, and aqueous HI for the acidic cleavage of ethers. What is the difference in the mechanisms and which will follow either of SN1/SN2 mechanism?
Once the ...
- 192
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1
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219
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Selectivity in dehydration of isopropyl alcohol to diisopropyl ether
Can isopropyl alcohol be dehydrated by sulfuric acid to diisopropyl ether in a similar way as to how ethanol can? Is there a way to avoid or at least minimize the inevitable dehydration to propylene?
user102173
3
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2
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111
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When does an aromatic ether break its bonds?
I was reading some reactions of ethers and I came across Zeisel determination. Later that day, I was asked to determine the products of the reaction :
And I made the product:
This reaction is ...
- 69
2
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0
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DEG monobutyl ether pH change
We are using DEG monobutyl ether (CAS 112-34-5) in our production. Normally it is pH neutral, however suddenly we noticed that it has shifted to being acidic (pH=3.4).
What has changed in the material?...
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2
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0
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Synthesis of allylic ether, starting with phenalene
I stumbled across a retro-synthesis question, for which I don't know the exact answer; I prepared two synthesis ways, but I don't know if they could be realized in a lab. The question is the following:...
user115162
0
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2
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Doubt in a question on cleavage of ethers (Solomons Practice problem 11.18) [closed]
I have reffered to the mechanism shown in the text which is:
But I am not able to figure out how this took place:
Please help me with it. Though it is a homework question but I have tried my best to ...
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0
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38
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What is the reaction mechanism involved in the ring opening seen in 3,3-diphenyloxiran-2-ide?
I have an epoxide with a negative (-) charge on one of the carbons. In which of the two ways should I open the epoxide? I am not able to understand which one to prefer.
(The general way I think of ...
- 1,389
4
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1
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293
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Which has higher priority between unsaturated ring and unsaturated chain in the nomenclature of organic compounds?
According to the IUPAC rules of nomenclature, alkenes have higher priority over rings but what if the ring also contains a double or a triple bond?
For eg:
Is this compound going to be named as 1-(2-...
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165
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Products of the reaction between ethoxyethene and HI
Problem
The products formed in the reaction
$$\ce{CH2=CHOCH2CH3 + HI ->}$$
are
(a) $\ce{CH2=CHI}$ and $\ce{CH3CH2I}$
(b) $\ce{CH2=CHI}$ and $\ce{CH3CH2OH}$
(c) $\ce{CH3CHO}$ and $\ce{CH3CH2I}$
(d) ...
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1
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142
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Why is the ether linkage breaking here?
I have been asked to find the major product of the following reaction:
This is my thought process: the lone pairs of the oxygen atom connected to $\ce{-Et}$ are less delocalised than the other oxygen ...
- 466
4
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0
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248
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What is the mechanism of benzyl ether hydrogenolysis?
The mechanism for the hydrogenation of alkenes or alkynes using Pd/C is fairly well explained to involve the absorption of hydrogen onto a metal's surface followed by the addition of that hydrogen ...
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2
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2
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892
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What are the products formed in acidic hydrolysis of a tetrahydropyranyl ester?
Find the major product of the following reaction:
My approach
From my knowledge of reagents, I figured out that that the acid will protonate the oxygen(s) in the reactant and after that $\ce{C-O \...
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votes
3
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496
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Synthesing tetrahydropyran from ethylene oxide
I thought that the first step must be using a Grignard reagent to add carbons, but I need a hydroxyl group on the carbon on the other side to make it a diol and produce the product given, but nothing ...
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1
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230
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Shape of PEG in water
According to the chemical formula $\ce{H−(O−CH2−CH2)_n−OH}$ of polyethylene glycol, or PEG, I assume that this organic compound has a long chain structure when it is dry and in powder form. (This is ...
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0
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286
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Reaction of multiple diols with sulphuric acid [closed]
Find the total number of possible products
I can think of atleast three reactions that will take place in the acidic medium:
Pinacol-Pinacolone rearrangement
Intermolecular dehydration (leading to ...
- 6,059
3
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1
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1k
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Why does H+ attack alkene first in this reaction?
The reaction is:
Why is the double bond attacked here even though it is in conjugation with the lone pairs of O thereby making it harder to extract. Also,don't the 2 lone pairs on OH have more ...
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1
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191
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Acidic cleavage of an ether
In the following question;
Apparently, an SN2 reaction ensues, where the iodine atom's supposed to cleave off with the less sterically hindered alkyl branch from both the oxygens. This is the ...
- 1,116
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1
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97
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Grignard alkoxide intermediate as starting material for ether or ester synthesis
I'm having a Grignard reaction between a ketone or aldehyde with RMgX in mind.
The average workup uses water to hydrolize the intermediate alkoxide. But could this intermediate be used without ...
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1
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507
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A reaction of Hydrogen Iodide and Ether
The problem is:
1,2,3-trimethoxy-cyclohexane reacts with $x$ moles of $\ce{HI}$ to give $y$ moles of $\ce{CH3I}$ and iodo-cyclohexane as product. Then find the value of $\frac{x+1}{y+1}$.
I am not ...
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1
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56
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Comparing between cleavage of ethers
We have to find out which ether would undergo cleavage faster.
My Attempt
IV. I couldn't figure out, so i carried out simple SN1 cleavage. Since +M effect of OH > OCH3 1st reactant seemed right ...
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1
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274
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Can Cyanide ion substitute methoxide? [closed]
Question
Attempt
Since CN is better nucleophile than both OMe and Cl, I believe that it should replace both. But none of the options match my answer. Where am I wrong? Please help.
- 603
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683
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Effect of substituents on arene oxide-phenol rearrangement
When I was learning about the reactions of epoxides from my textbook, I came across the following mechanism for arene oxide-phenol rearrangement in the presence of acid:
NIH Shift - National ...
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12
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1
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167
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The Evasive Ether: Existence of diethynyl ether?
I tried to find online whether the compound diethynyl ether, $\ce{HC#COC#CH}$, exists in a stable state at STP, mainly out of curiosity, but also because it would be interesting to study the ...
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4
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Reactivity of different alcohols with NaNH2 and CH3I
Identify the final product (B) in the following reaction:
I'm not sure how $\ce{NaNH2}$ and $\ce{CH3I}$ will react with the different types of alcohol present here. According to my solution,ether was ...
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0
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107
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Why can't strong bases cleave ethers?
I'm imagining a strong base like NaNH2 attacking the adjacent carbon of the ether, giving the oxygen a lone pair and forming an alkoxide. NH3 has a pKa of 36 while an alcohols (conjugate acid of ...
1
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0
answers
27
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Benzannulation of 18-crown-6
I know crown ethers can be used to complex metal ions.
Question: What important properties do 18-crown-6 change during the benzannulation from 18-crown-6 to DB18C6 (dibenzo-18-crown-6)? How do these ...
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0
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69
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Do tertiary ethers tolerate oxidative workup of an ozonolysis reaction?
I am attempting to cleave a double bond into a carboxylic acid and carbon dioxide using an ozonolysis reaction followed by an oxidative workup. I am concerned with the presence of a tertiary ether in ...
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1
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Reaction of ether with HCl
Most of the reactions undergo ring expansion whenever favourable.
But this reaction [1, p. 514] doesn't seems to do so:
Practice Problem 11.18 Provide a mechanism for the following reaction.
Could ...
3
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3
answers
4k
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How many ether metamers are possible for C4H10O?
How many ether metamers are possible for $\ce{C4H10O}?$
According to me, the answer should be 2 but it was given 3. I know 3 structures can be made:
$$\ce{CH3—O—CH2—CH2—CH3}\tag{1}$$
$$\ce{CH3—CH2—...
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2
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Acidic cleavage of ether with a 2° alkyl group
I know that an ether with a 3° alkyl group and a 1° alkyl group is cleaved by $\mathrm{S_N1}$ mechanism to give a tertiary alkyl halide and a 1° alcohol.
And an ether with a two 1° alkyl groups is ...
1
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0
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56
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What lubricant can be used for mechanical parts in a system containing diethyl ether?
I make a thermal actuator that works with the expansion of diethyl ether at its boiling point of around 34 °C. For sealing and lubrication of the polypropylene piston and barrel, I need a lubricant ...
- 11
6
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2
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2k
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Is cyclic ether oxidised by periodic acid?
Is the three member ring of cyclic ether oxidised by periodic acid? As this also has oxygen attached to adjacent carbon so I think that cyclic ether of three members should be oxidised by periodic ...
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954
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Role of zinc chloride in reaction of ether
I am trying to do a reaction between acetyl chloride $\ce{CH3COCl}$ with diethyl ether. I know that upon using anhydrous $\ce{ZnCl2}$ and heat, I'll get an ester and an alkyl chloride, but I'm not ...
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Which one is the stronger Lewis base: diethyl ether or tetrahydrofuran?
I am trying to understand Lewis bases (bear with me, I am a physicist). I was asking myself how diethyl ether and tetrahydrofuran compare with respect to their properties as solvents in electrophilic ...
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0
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158
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Ethyl Acetate and other Solvents in a mixture: miscibility and stability
I was wondering about a heterogeneous solvent mixture containing multiple alcohols such as IPA, Ethanol, methanol etc. Would EtOAc (Ethyl Acetate) play nice in these mixtures at low volumes such as 1 ...
- 1
1
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2
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3k
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Using TBAI (tetra-butylammonium iodide) as a catalyst. Ideas on the mechanism or the driving force?
for my etherification of an alcoxide with alkylbromide I used TBAI as a catalyst. The catalyst transfers the alkylbromide into an alkyliodide which is more reactive.
I was wondering, what is the ...
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1
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30
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Opening of ethers using acids [closed]
I got that following my solution i get the product is 3HCO2H
but the given answer is 3HCHO
-1
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1
answer
53
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How to check leaving group ability of cations?
In the reaction of an ether with a hydrogen halide (HX), the positive hydrogen ion replaces one of the alkyl groups attatched to the oxygen; but why does this happen, isn't the hydrogen ion a better ...
- 13
2
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0
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254
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Addition of NaBH4 and LiAlH4
NaBH4 and LiAlH4 will be a source for the hydride ion and reaction will begin with addition of hydride by displacing the carbonyl group.
But I am not sure will it attack both the carbonyl or only one....
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2
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0
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65
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Deperoxidation of ethers via alumina: what happens?
I was reading about the procedures for the removal of peroxides from ethereal solvents, and a procedure which seems to have survived to our days is filtration through a column of "activated alumina" (...
user32223
-2
votes
1
answer
59
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Nucleophilic comparison of epoxides and ketones [closed]
Why does $\ce{H+}$ attack on epoxide and not on the double bonded oxygen?
- 9
8
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1
answer
329
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Are crown ethers "recycled", typically?
I know that crown ethers have the interesting property of strongly complexing alkali metals, which allows them to be used in organic solvents (eg. as "dissolving-activity enhancing agents" for ...
user32223
8
votes
2
answers
2k
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Claisen rearrangement in substituted ring
This is an example of Claisen rearrangement, property of allyl vinyl/phenyl ethers.
I believe that the allylic migration should take place to the position ortho to both $\ce{-CH3}$ and $-\ce{OR}$ ...
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