Thionyl Chloride → 2-(4-Chlorophenyl)ethyl chloride

Temperature

67.5 °C

Into a 250-mL round-bottom flask equipped with magnetic stirring, a thermocouple, a condenser, and a nitrogen bubbler vented to caustic scrubber, was charged 2-(4-chlorophenyl)ethanol (25.119 g, 160 mmol), toluene (73 mL) and N,N-dimethylacetamide (0.751 ml, 8.02 mmol). The mixture was heated in oil bath to between 65 and 70° C. and thionyl chloride (12.29 ml, 168 mmol) was charged over 1 h with a maximum reaction temperature of 69° C. The reaction was then stirred for 2 h at 65 to 70° C. The resulting dark-brown solution was cooled to 40° C. and washed with water (2×40 mL) by stirring for 2-5 min at 45° C. (bath) and separating the phases at room temperature. The organic phase was further washed with saturated aqueous sodium bicarbonate solution (3×40 mL) by stirring for 2-5 min at 50° C. (bath) and separating the phases at room temperature.

1. customInto a 250-mL round-bottom flask equipped with magnetic stirring
2. temperatureThe mixture was heated in oil bath to between 65 and 70° C.
3. temperatureThe resulting dark-brown solution was cooled to 40° C.
4. washwashed with water (2×40 mL)
5. stirringby stirring for 2-5 min at 45° C. (bath)
6. customseparating the phases at room temperature
7. washThe organic phase was further washed with saturated aqueous sodium bicarbonate solution (3×40 mL)
8. stirringby stirring for 2-5 min at 50° C. (bath)
9. customseparating the phases at room temperature

ORD record

ord-91836356a659470085baddd397d7ee25

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08952197B2