Methanol → Methyl (2-chlorophenyl)acetate

HRID 1766032Notes

Reaction equation

HRID 1766032 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([OH:11])=[O:10].[CH3:12]O>S(=O)(=O)(O)O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([O:11][CH3:12])=[O:10]

Participants

4

Reactant 2

HCID 887MethanolHCID 17124o-Chlorophenylacetic acid

Product 1

HCID 93683Methyl (2-chlorophenyl)acetateYield 97.5%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

To 2-chlorophenylacetic acid (1.04 g, 6 mmol) in MeOH (25 mL) was added sulfuric acid (6 drops) and the solution was refluxed for 16 hours. After concentration, the residue was taken up in ethyl acetate and washed with sat'd aq. NaHCO3, H2O and brine. The organic layer was dried over Na2SO4 and concentrated to give methyl (2-chlorophenyl)acetate 2a (1.08 g, 97.5%) as a yellowish oil. GCMS (EI) m/z 184, 186 (M+).

Workup

  1. temperaturethe solution was refluxed for 16 hours
  2. concentrationAfter concentration
  3. washwashed with sat'd aq. NaHCO3, H2O and brine
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-83aa81ec95d54a3894cfdc4d7446020d
Source dataset
uspto-grants-2007_06
Patent number
US07229995B2

Reaction notes

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