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

HRID 2214007Notes

Reaction equation

HRID 2214007 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-51a8baa3523545cb8832912b31d8f267
Source dataset
uspto-grants-2006_09
Patent number
US07105671B2

Reaction notes

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