Hydrogen Peroxide → 2-Cyclopropyl-2-(4-chlorophenyl)ethanol

Temperature

0 °C

Under a nitrogen atmosphere, a stirred solution of 3.5 grams (0.019 mole) of 1-cyclopropyl-1-(4-chlorophenyl)ethene in 10 mL of distilled tetrahydrofuran was cooled to 0° C., and 29.5 mL (0.020 mole) of 0.68S M bis(3-methyl-2-butyl)borane in tetrahydrofuran was added via syringe during a 10 minute period. Upon completion of addition, the reaction mixture was stirred at 0° C. for 1.3 hours, at ambient temperature for 2.5 hours, and at 60° C. for 0.75 hour. The reaction mixture was cooled to 0° C., and 17 mL of methanol, 8.8 mL of aqueous 10% sodium hydroxide solution, and 8.0 mL of aqueous 30% hydrogen peroxide solution were sequentially added. Upon completion of addition, the reaction mixture was stirred at ambient temperature for 18 hours. The reaction mixture was heated at 60° C. for 30 minutes and then was cooled, after which 30 mL of an aqueous solution saturated with potassium carbonate was added. The aqueous layer was separated and extracted with three 30 mL portions of diethyl ether. The organic materials were combined and washed with 30 mL of an aqueous, saturated potassium carbonate solution. The organic layer was dried with magnesium sulfate/potassium carbonate and filtered. The filtrate was concentrated under reduced pressure, yielding 3.8 grams of 2-cyclopropyl- 2-(4-chlorophenyl)ethanol. The nmr and ir spectra were consistent with the proposed structure.

1. additionUpon completion of addition
2. waitat 60° C. for 0.75 hour
3. temperatureThe reaction mixture was cooled to 0° C.
4. additionUpon completion of addition
5. stirringthe reaction mixture was stirred at ambient temperature for 18 hours
6. temperatureThe reaction mixture was heated at 60° C. for 30 minutes
7. temperaturewas cooled
8. customThe aqueous layer was separated
9. extractionextracted with three 30 mL portions of diethyl ether
10. washwashed with 30 mL of an aqueous, saturated potassium carbonate solution
11. dry with materialThe organic layer was dried with magnesium sulfate/potassium carbonate
12. filtrationfiltered
13. concentrationThe filtrate was concentrated under reduced pressure

ORD record

ord-6a5579bf2f36452eae874283363b1bfd

Source dataset

uspto-grants-1989_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04808762