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

HRID 1957939Notes

Reaction equation

HRID 1957939 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>>[CH2:16]([O:15][C:13](=[O:14])[CH2:12][C:6]1[CH:11]=[CH:10][C:9]([S:2]([Cl:1])(=[O:5])=[O:3])=[CH:8][CH:7]=1)[CH3:17]

Participants

3

Reactant 2

HCID 7590Ethyl phenylacetateHCID 24638Chlorosulfonic acid

Product 1

HCID 10467900(4-Chlorosulfonyl-phenyl)-acetic acid ethyl esterYield 56.3%

Conditions

Temperature
40 °C

Procedure

The chlorosulfonic acid (16.6 mL, 250 mmol) was added dropwise into ethyl phenylacetate (8.2 g, 50 mmol) under stirring at 40° C. Thereafter, the mixture was stirred for 0.5 hour at room temperature, and then poured on ice and extracted with dichloromethane. The combined organic phase was washed by saline, dried with sodium sulfate and concentrated under reduced pressure. The concentrate was separated through column chromatography (petroleum ether/ethyl acetate=6/1, v/v) to obtain yellow oil (7.4 g, yield: 56%).

Workup

  1. stirringThereafter, the mixture was stirred for 0.5 hour at room temperature
  2. additionpoured on ice
  3. extractionextracted with dichloromethane
  4. washThe combined organic phase was washed by saline
  5. dry with materialdried with sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe concentrate was separated through column chromatography (petroleum ether/ethyl acetate=6/1

Sources & evidence

ORD record
ord-9bd4a204d30d43f1acb4bd26ce5b8560
Source dataset
uspto-grants-2013_04
Patent number
US08410094B2

Reaction notes

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