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Topic: Preparation of 3-hydroxyacetophenone  (Read 4491 times)

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Offline Rutherford

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Preparation of 3-hydroxyacetophenone
« on: October 19, 2012, 12:58:57 PM »
Is it possible to prepare 3-hydroxyacetophenone from the reaction between phenol, acetylchloride and AlCl3?

OH group wants to push the incoming group to "o" and "p" positions, but meta will be made, too, at least in traces, so I would say yes, but the answer is no. Why?
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Offline discodermolide

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Re: Preparation of 3-hydroxyacetophenone
« Reply #1 on: October 19, 2012, 01:02:42 PM »
Because the phenolic OH will be acylated and in the presence of AlCl3 will undergo a Fries rearrangement.

http://en.wikipedia.org/wiki/Fries_rearrangement
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Offline Rutherford

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Re: Preparation of 3-hydroxyacetophenone
« Reply #2 on: October 19, 2012, 01:38:19 PM »
If I understood well, this reaction makes the preparation impossible:
CH3COCl+C6H5OH :rarrow: HCl+C6H5COCH3
Then goes the Fries rearrangement.
Thanks for the answer.
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Offline discodermolide

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Re: Preparation of 3-hydroxyacetophenone
« Reply #3 on: October 19, 2012, 01:40:45 PM »
My pleasure.
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