Methanol → Methyl (2-chlorophenyl)acetate

HRID 1744290Notes

Reaction equation

HRID 1744290 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+). Step 2B: Preparation of Methyl 2-(2-chlorophenyl)-3-(dimethylamino)acrylate 2b

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-da61025c479c40deb24e8dc1737c693b
Source dataset
uspto-grants-2006_03
Patent number
US07015226B2

Reaction notes

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