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Can someone confirm that this is a correct way to make 2-butanol starting from 2-propanol?

  1. First add Cl2 and UV-light to it to become 1-chloro-2-propanol

  2. Make from CH3Cl a Grignard reagent by adding Mg and dry ether

  3. Let a nucleophile substitution happen between CH3MgCl and 1-chloro-2-propanol

  4. You get 2-butanol?

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I would not do that.

  1. Radical chlorination is inherently unselective because of the high reactivity of the chlorine radical, if you have to propose this as part of a synthetic route there's a 99% chance you're not doing it right

  2. Your Grignard will get immediately destroyed by the hydroxyl group present

  3. Grignard SN2 reactions on alkyl halides don't go very well either

Off the top of my head, I would think a much better way would be to oxidise the starting material to acetone, make an enolate with LDA, do a SN2 with MeI, and reduce the compound back with NaBH4.

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  • $\begingroup$ Methyl iodide would probably be attacked by the oxygen and lead to a methyl-vinyl-ether. $\endgroup$
    – Jan
    Commented Nov 2, 2016 at 2:05

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