Thionyl Chloride → 4-(2-Chloroethyl)phenyl methyl ether
Reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([CH2:7][CH2:8]O)=[CH:5][CH:4]=1.S(Cl)([Cl:14])=O>ClCCl.[Cl-].[Na+].O>[Cl:14][CH2:8][CH2:7][C:6]1[CH:10]=[CH:11][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
4-methoxy-phenethyl alcohol (15.2 g, 10 mmol) were dissolved in 200 ml of dichloromethane and at 0° C., 7.35 ml of thionyl chloride were added. The reaction mixture was allowed to warm to room temperature over 1/2 hour. After stirring for 20 hours, the mixture was added to brine and extracted with dichloromethane. The dichloromethane was evaporated to obtain an oil which was chromatographed on silica gel using a mixture of 30% ethyl acetate/hexane as the eluent to obtain 8.8 g (51%) of the title product.
Workup
- extractionextracted with dichloromethane
- customThe dichloromethane was evaporated
- customto obtain an oil which
- customwas chromatographed on silica gel using
- additiona mixture of 30% ethyl acetate/hexane as the eluent
Sources & evidence
- ORD record
- ord-3108fabd02d34a17998757fd77927f83
- Source dataset
- uspto-grants-1997_04
- Patent number
- US05618793
Reaction notes
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