Ethyl phenylacetate → (4-Chlorosulfonyl-phenyl)-acetic acid ethyl ester

HRID 618760Notes

Reaction equation

HRID 618760 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[C:6]1([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>>[Cl:1][S:2]([C:9]1[CH:10]=[CH:11][C:6]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:7][CH:8]=1)(=[O:5])=[O:3]

Participants

3

Reactant 2

HCID 7590Ethyl phenylacetateHCID 24638Chlorosulfonic acid

Product 1

HCID 10467900(4-Chlorosulfonyl-phenyl)-acetic acid ethyl ester

Conditions

Temperature
40 °C

Procedure

Chlorosulfonic acid (87 ml) was added dropwise to ethyl phenylacetate (48 g), and the mixture was stirred at 40° C. for 30 minutes. The reaction mixture was poured into ice water (1000 ml), and the separated oily substance was extracted with methylene chloride. The methylene chloride layer was washed successively with water and a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. Evaporation of the solvent under reduced pressure gave ethyl 4-chlorosulfonylphenylacetate (42 g).

Workup

  1. extractionthe separated oily substance was extracted with methylene chloride
  2. washThe methylene chloride layer was washed successively with water
  3. dry with materiala saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate
  4. customEvaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-a8ab4aa416194c1dbdf66882f42980f9
Source dataset
uspto-grants-1999_09
Patent number
US05955505

Reaction notes

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