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

HRID 1689233Notes

Reaction equation

HRID 1689233 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-ce9990a37c88407e9dcd9797da95d28b
Source dataset
uspto-grants-2012_04
Patent number
US08148373B2

Reaction notes

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