Methanol → Methyl (2-chlorophenyl)acetate

HRID 347780

Reaction equation

HRID 347780 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 6a (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-3743fead2e244e8f877581d62ad96443
Source dataset
uspto-grants-2007_02
Patent number
US07176211B2

Linked notes

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