January 15, 2025, 10:27:43 AM
Forum Rules: Read This Before Posting


« previous next »
Pages: [1]   Go Down

Topic: Preparation of 3-hydroxyacetophenone  (Read 4525 times)

0 Members and 1 Guest are viewing this topic.

Offline Rutherford

  • Sr. Member
  • *****
  • Posts: 1868
  • Mole Snacks: +60/-29
  • Gender: Male
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?
Logged

Offline discodermolide

  • Chemist
  • Sr. Member
  • *
  • Posts: 5038
  • Mole Snacks: +405/-70
  • Gender: Male
    • My research history
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
Logged
Development Chemists do it on Scale, Research Chemists just do it!
My Research History

Offline Rutherford

  • Sr. Member
  • *****
  • Posts: 1868
  • Mole Snacks: +60/-29
  • Gender: Male
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.
Logged

Offline discodermolide

  • Chemist
  • Sr. Member
  • *
  • Posts: 5038
  • Mole Snacks: +405/-70
  • Gender: Male
    • My research history
Re: Preparation of 3-hydroxyacetophenone
« Reply #3 on: October 19, 2012, 01:40:45 PM »
My pleasure.
Logged
Development Chemists do it on Scale, Research Chemists just do it!
My Research History
Pages: [1]   Go Up
« previous next »
Sponsored Links