Re: ORGLIST:acetylation

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From: V P (vpnagarajan5$##$yahoo.com)
Date: Sat Jan 24 2004 - 06:47:42 EST

Hope the attached info. may be of some help to you.
Nagaorajan

sanjeev kumar vernekar <vvsanjeev$##$rediffmail.com> wrote:

Dear all,
    I am working on carbohydrates ,i am facing problem with acetylation of tertiary and hinderd hydroxy group.I have tried with many reported procedures (with DMAP and all) nothing is working if any one has idea how to acetylate hindered teriary hydroxy group,please let me know.looking forward to here from you .
regards
sanjeev.
Sanjeev Kumar Vernekar
Institute for organic chemistry,
correnstrass -40
muenster
Germany-48151
Ph- 0049 251 2033748

 

Regards,
 
Nagaorajan

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Acetylation of Mesitol

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Acetylation of Mesitol - DMAP as Catalyst

G. Hoefle and W. Steglich, Synthesis, 619 (1972)

  1. To a solution of mesitol (1.36 g, 10 mmol), and DMAP (1.5 g, 12 mmol) in dichloromethane (10 mL) is added acetic anhydride (1.3 g, 13 mmol).

  2. An exothermic reaction ensues, and after 2 h, addition of methanol and evaporation of the solvents gives an oily residue.

  3. The residue is suspended in ether and successively washed with 2 N hydrochloric acid and aqueous sodium bicarbonate solution.  The ether layer is dried (anhydrous magnesium sulfate), filtered, and evaporated to afford 2,4,6-trimethylphenyl acetate (1.75 g, 98%).

Click on Keywords below to see other related reactions:

Acylation

Acetylation

Phenol

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