Methanol → Methyl 2-(3,4-dichlorophenyl)acetate

HRID 854718Notes

Reaction equation

HRID 854718 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([OH:12])=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8].S(=O)(=O)(O)O.[CH3:18]O>>[CH3:18][O:11][C:10](=[O:12])[CH2:9][C:4]1[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 798743,4-Dichlorophenylacetic acid

Product 1

HCID 1268257Methyl 2-(3,4-dichlorophenyl)acetate

Procedure

A solution of (3,4-dichloro-phenyl)-acetic acid (14.0 g, 0.07 mol) in methanol (71 mL) was treated with a catalytic amount of concentrated sulfuric acid. The reaction mixture was heated under reflux for 12 h. The reaction was concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 50/50 hexanes/ethyl acetate) afforded (3,4-dichloro-phenyl)-acetic acid methyl ester (15.0 g, quant.) as a white solid: mp 30-32° C.; EI-HRMS m/e calcd for C9H8Cl2O2 (M+) 217.9901. found 217.9907.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 12 h
  3. concentrationThe reaction was concentrated in vacuo

Sources & evidence

ORD record
ord-36dccf012e2f4dbd94b169064fa9a215
Source dataset
uspto-grants-2007_08
Patent number
US07259166B2

Reaction notes

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