Thionyl Chloride → HCID 13948363, compound
Reaction equation
O[CH2:2][CH:3]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:4]([O:6][CH2:7][CH3:8])=[O:5].O=S(Cl)[Cl:17].C(=O)(O)[O-].[Na+]>ClCCl>[Cl:17][CH2:2][CH:3]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:4]([O:6][CH2:7][CH3:8])=[O:5]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To ethyl 3-hydroxy-2-phenylpropionate (2.55 g, 13.1 mmol) in dichloromethane (15 ml), SOCl2 (1.87 g, 15.7 mmol) in dichloromethane (1 ml) was added while chilling with ice. After the resulting solution was stirred to cause reaction at room temperature for 3 hours, saturated aqueous sodium bicarbonate was added while chilling with ice. The prepared solution was extracted with dichloromethane, and the extract was washed with saturated aqueous sodium chloride, and then dried over anhydrous sodium sulfate. Subsequently, the solvent was removed by distillation under reduced pressure to obtain a crude product. The product was purified by silica gel column chromatography using acetone/hexane=1/3 to obtain 1.27 g of the titled compound as a colorless oil (yield: 45.5%).
Workup
- temperaturewhile chilling with ice
- customreaction at room temperature for 3 hours
- temperaturewhile chilling with ice
- extractionThe prepared solution was extracted with dichloromethane
- washthe extract was washed with saturated aqueous sodium chloride
- dry with materialdried over anhydrous sodium sulfate
- customSubsequently, the solvent was removed by distillation under reduced pressure
- customto obtain a crude product
- customThe product was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-0217eb779eb64be4bb10f3b942e172bb
- Source dataset
- uspto-grants-1998_12
- Patent number
- US05852006
Reaction notes
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