Methanol → Methyl 2-(3-chlorophenyl)acetate

HRID 2172711Notes

Reaction equation

HRID 2172711 reaction equation
S(Cl)(Cl)=O.[Cl:5][C:6]1[CH:7]=[C:8]([CH2:12][C:13]([OH:15])=[O:14])[CH:9]=[CH:10][CH:11]=1.[CH3:16]O>>[Cl:5][C:6]1[CH:7]=[C:8]([CH2:12][C:13]([O:15][CH3:16])=[O:14])[CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 158793-Chlorophenylacetic acidHCID 24386Thionyl Chloride

Product 1

HCID 2733544Methyl 2-(3-chlorophenyl)acetate

Conditions

Temperature
80 °C

Procedure

Thionyl chloride (11 g, 100 mmol) was added dropwise to a mixture of 3-chlorophenylacetic acid (1.7 g, 10 mmol) in methanol (20 mL) at 0° C. The resulting mixture was refluxed at 80° C. for 12 hours. The volatiles were removed under vacuum and the residue was diluted with water and extracted with ethyl acetate. The combined organic solution was washed with water, dried over sodium sulfate and the concentrated to give 1.5 g of methyl 2-(3-chlorophenyl)acetate as a yellow oil, which was used without further purification.

Workup

  1. customThe volatiles were removed under vacuum
  2. additionthe residue was diluted with water
  3. extractionextracted with ethyl acetate
  4. washThe combined organic solution was washed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationthe concentrated

Sources & evidence

ORD record
ord-fd51bb56e0ea43a9b814d7a2c940b3d8
Source dataset
uspto-grants-2015_06
Patent number
US09056852B2

Reaction notes

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