Sulfuric Acid → Methyl (2-chlorophenyl)acetate

HRID 1986871Notes

Reaction equation

HRID 1986871 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].[CH:12](OC)(OC)OC.OS(O)(=O)=O>CO.CCOC(C)=O>[CH3:12][O:10][C:9](=[O:11])[CH2:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[Cl:1]

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 9005Trimethyl orthoformateHCID 17124o-Chlorophenylacetic acid

Product 1

HCID 93683Methyl (2-chlorophenyl)acetateYield 97.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 10.0 g (59 mmol) (2-chlorophenyl)acetic acid in MeOH (10 mL) was added 9.6 mL (88 mmol) of trimethyl orthoformate and 0.32 mL (6.0 mmol) of H2SO4. The reaction was stirred at room temperature for 4 h then diluted with EtOAc and washed with H2O followed by a saturated aqueous solution of NaHCO3. The organic phase was dried over anhydrous Na2SO4 and concentrated under reduced pressure to provide 10.6 g (97%) of (2-chlorophenyl)-acetic acid methyl ester as a clear oil. The crude reaction product was not purified but used immediately.

Workup

  1. washwashed with H2O
  2. dry with materialThe organic phase was dried over anhydrous Na2SO4
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5e99ee216e694cd1a258d9782dcd7874
Source dataset
uspto-grants-2009_06
Patent number
US07550473B2

Reaction notes

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