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.CN(C)C(=O)C.S(Cl)([Cl:19])=O>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][Cl:19])=[CH:4][CH:3]=1Participants
4
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 (25.033 g, 160 mmol). N,N-Dimethylacetamide (0.749 mL, 7.99 mmol) was added and the mixture was heated in oil bath to 58° C. Thionyl Chloride (12.25 mL, 168 mmol) was charged over 1 h while the reaction temperature was maintained at <66° C. The resulting brown solution was stirred at 60 to 64° C. for 2.5 h and then allowed to gradually cool to room temperature leaving a dark brown oil.
Workup
- customInto a 250-mL round-bottom flask equipped with magnetic stirring
- temperaturewas maintained at <66° C
- temperatureto gradually cool to room temperature
- customleaving a dark brown oil
Sources & evidence
- ORD record
- ord-997da2f797cd458f8d454066e7b528a1
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08952197B2
Reaction notes
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