# Is a Methoxy group meta directing in this problem?

The following question was given in chemistry today , August 2020 edition , page 47 , problem 9. The answer to this problem is (a).

My Attempt

In the third step , the carbon electrophile can attack at ortho position to carbon substituent to give a 6 membered ring.

But , the O-Methyl group is ortho para directing. The resonance structures are as follows.

The given answer is , a , is possible only if we consider O-Methyl group on Benzene as meta directing group.

My Question:

Is methoxy group on ANISOLE Meta directing ?

• The presence of the OMe activates the whole ring to electrophilic attack. The o & p positions are most activated but m is also activated. Your attempted mechanism is correct Nov 19 '20 at 8:05
• Anisole is a whole. The question in the last line is wrong in terms, Even if we know what you mean. Nov 19 '20 at 8:16
• My question is how did the CH2 group para to the methoxy shift to a meta position? Unless this question represents a surprising mechanism, answer d seems to make the most sense. Nov 19 '20 at 14:26
• I agree, d is the product Nov 19 '20 at 14:30
• Are you not concerned how an E-double bond becomes Z in the cyclized product? Nov 19 '20 at 15:58

(E)-Acyl chloride 1 must rotate about the red β-γ single bond and $$\ce{AlCl3}$$ must complex with the carbonyl oxygen forming species 2. [One may also invoke $$\ce{AlCl3}$$ complexation with the chlorine and rationalize the subsequent steps via an acylium ion and conjugated ketenes. The principle is the same.] Loss of a proton at the γ-position of conformation 2 provides the β,γ-(Z)-double bond of 3. Now deconjugated acyl chloride 4 is ready for F-C cyclization to intermediate 7 and onto 7-methoxynaphthalen-1-ol (9), aka (d). Alternatively, rotation about the red bond in 3 leads to conformation 5, which, upon γ-protonation leads to α,β-(Z)-conjugated acyl chloride 6. Subsequent F-C cyclization via intermediate 8 affords 9. Incidently, base is not required to produce 9 from 7 or 8. F-C conditions are sufficient.