Methanol → Methyl 2-(3-chlorophenyl)acetate

HRID 350436

Reaction equation

HRID 350436 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.[CH3:12]O.OS(O)(=O)=O>ClC(Cl)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 158793-Chlorophenylacetic acid

Product 1

HCID 2733544Methyl 2-(3-chlorophenyl)acetateYield 107.8%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 3-chlorophenylacetic acid (21.76 g, 127.6 mmol) in dichloroethane (100 ml) was added MeOH (15:6 ml, 383 mmol) and H2SO4 (1 ml) at room temperature. After 20 minutes stirring, the mixture was heated at 80° C. for 2 h. The reaction mixture was poured into ice water and extracted with CHCl3. The combined extracts were washed with aq. NaHCO3 and brine. After dried over Na2SO4, the extract was concentrated in vacuo to give methyl 3-chlorophenylacetate (25.4 g, 100%) as a colorless oil. 1H-NMR (CDCl3) δ 3.60 (s, 2H), 3.70 (s, 3H), 7.15–7.26 (m, 4H).

Workup

  1. extractionextracted with CHCl3
  2. washThe combined extracts were washed with aq. NaHCO3 and brine
  3. dry with materialAfter dried over Na2SO4
  4. concentrationthe extract was concentrated in vacuo

Sources & evidence

ORD record
ord-58c61a5b79d44fc78fd27a8646da9633
Source dataset
uspto-grants-2007_02
Patent number
US07179819B2

Linked notes

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