Acetyl chloride → Methyl 3-Hydroxyphenylacetate

HRID 1833241Notes

Reaction equation

HRID 1833241 reaction equation
[C:1](Cl)(=O)C.[OH:5][C:6]1[CH:7]=[C:8]([CH2:12][C:13]([OH:15])=[O:14])[CH:9]=[CH:10][CH:11]=1>CO>[CH3:1][O:14][C:13](=[O:15])[CH2:12][C:8]1[CH:9]=[CH:10][CH:11]=[C:6]([OH:5])[CH:7]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 121223'-Hydroxyphenylacetic acid

Product 1

HCID 39129Methyl 3-HydroxyphenylacetateYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To methanol (300 mL) was added acetyl chloride (8.9 mL) dropwise in 10 minutes with stirring. 3-Hydroxyphenylacetic acid (25 g, 164 mmol) was added to the mixture at one time. The reaction mixture was stirred at room temperature for 15 hrs. The solvent was evaporated and the residue was concentrated in vacuo to afford 3-hydroxyphenyl acetic acid methyl ester (27.3 g, 99% yield) as a red oil.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 15 hrs
  2. customThe solvent was evaporated
  3. concentrationthe residue was concentrated in vacuo

Sources & evidence

ORD record
ord-886c255d91954c04bd5c2784b26d863f
Source dataset
uspto-grants-2006_06
Patent number
US07067529B2

Reaction notes

Loading…