Thionyl Chloride → 2-(4-Chlorophenyl)ethyl chloride
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9]O)=[CH:4][CH:3]=1.S(Cl)([Cl:13])=O>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][Cl:13])=[CH:4][CH:3]=1Participants
3
Conditions
- Temperature
- 58 °C
Procedure
Into a 250-mL round-bottom flask equipped with magnetic stirring, a thermocouple, a condenser, and a nitrogen bubbler vented to a caustic scrubber, was charged 2-(4-chlorophenyl)ethanol (25.026 g, 160 mmol) N,N-dimethylformamide (0.621 mL, 7.99 mmol) was added and the mixture was heated to 58° C. Thionyl Chloride (12.25 mL, 168 mmol) was charged over 1 h while the temperature was maintained at <65° C. Upon completion of the addition, the mixture was stirred at 60 to 64° C. for 2.5 h, and then allowed to gradually cool to room temperature and stirred overnight to give a clear, golden oil.
Workup
- customInto a 250-mL round-bottom flask equipped with magnetic stirring
- additionwas added
- temperaturewas maintained at <65° C
- additionUpon completion of the addition
- temperatureto gradually cool to room temperature
- stirringstirred overnight
- customto give a clear, golden oil
Sources & evidence
- ORD record
- ord-792ab8a9514e46a6bfb6547e355ea2cb
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08952197B2
Reaction notes
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