Ethyl phenylacetate → (4-Chlorosulfonyl-phenyl)-acetic acid ethyl ester
Reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[CH2:6]([O:8][C:9](=[O:17])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:7]>[Cl-].[Na+]>[CH2:6]([O:8][C:9](=[O:17])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([S:2]([Cl:1])(=[O:5])=[O:3])=[CH:13][CH:12]=1)[CH3:7]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
To a cooled chlorosulfonic acid (83.83 g, 48 mL, 0.71 mol) under nitrogen is added the title A compound, phenylacetic acid ethyl ester (59 g, 0.35 mol) over a period of 1 h. Reaction temperature is brought to RT (28° C.), then heated to 70° C., maintaining it at this temperature for 1 h while stirring. Reaction is cooled to RT and poured over saturated aqueous sodium chloride solution (200 mL) followed by extraction with DCM (2×200 mL). The organic layer is washed with water (5×100 mL), followed by saturated aqueous sodium chloride solution (1×150 mL). The organic layer dried over sodium sulfate, filtered and concentrated in vacuo to give crude (4-chlorosulfonyl-phenyl)acetic acid ethyl ester. Further column chromatography over silica gel (60-120 mesh), using 100% hexane afforded pure (4-chlorosulfonyl-phenyl)-acetic acid ethyl ester as a colorless oil.
Workup
- customReaction temperature
- customis brought to RT
- custom(28° C.)
- temperaturemaintaining it at this temperature for 1 h
- customReaction
- temperatureis cooled to RT
- extractionfollowed by extraction with DCM (2×200 mL)
- washThe organic layer is washed with water (5×100 mL)
- dry with materialThe organic layer dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-79d4dbafef804a65852744ba59e41604
- Source dataset
- uspto-grants-2010_07
- Patent number
- US07750020B2
Reaction notes
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