Acetyl chloride → Methyl 4-hydroxy-2,5-dimethylbenzoate

HRID 471002Notes

Reaction equation

HRID 471002 reaction equation
[C:1](Cl)(=O)C.[OH:5][C:6]1[C:14]([CH3:15])=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[C:8]([CH3:16])[CH:7]=1>CO>[OH:5][C:6]1[C:14]([CH3:15])=[CH:13][C:9]([C:10]([O:12][CH3:1])=[O:11])=[C:8]([CH3:16])[CH:7]=1

Participants

4

Reactant 2

HCID 6367Acetyl chloride2×HCID 236001494-Hydroxy-2,5-dimethylbenzoic acid

Product 1

HCID 22615980Methyl 4-hydroxy-2,5-dimethylbenzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Acetyl chloride (0.107 mL) was added dropwise to a solution of 4-hydroxy-2,5-dimethylbenzoic acid (example 18, step a) (0.249 g) in methanol (15 mL) and the resulting mixture stirred at room temperature for 72 h. Acetyl chloride (0.107 mL) was then added and the reaction heated to 50° C. and stirred at this temperature overnight. The reaction was concentrated and the residue purified by silica gel chromatography eluting with 1:1 isohexane:ethyl acetate to 100% ethyl acetate gradient. The fractions containing product were combined and evaporated in vacuo to give the subtitled compound as a white solid. Yield 0.25 g.

Workup

  1. temperaturethe reaction heated to 50° C.
  2. stirringstirred at this temperature overnight
  3. concentrationThe reaction was concentrated
  4. customthe residue purified by silica gel chromatography
  5. washeluting with 1:1 isohexane
  6. additionThe fractions containing product
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-996f9c70731d4b318e277e7bb19e922a
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Reaction notes

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