Methanol → Methyl 2-(3-chlorophenyl)acetate

HRID 354372Notes

Reaction equation

HRID 354372 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) δ3.60 (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-0a2defb579d449558261c7a696e581b3
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Reaction notes

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