Cyclohexanone → 1-Allyl-1-cyclohexanol

A solution of allyl magnesium bromide in diethyl ether (1 M, 53 mL, 53 mmol) was added dropwise to a solution of cyclohexanone (5.00 mL, 48.2 mmol) in diethyl ether at 0° C. The cloudy white reaction mixture was allowed to stir at rt overnight. The reaction was quenched with saturated aqueous NH4Cl (100 mL) and diluted with water (20 mL) and diethyl ether (50 mL). The mixture was transferred to a separatory funnel and the layers were separated. The aqueous layer was extracted with diethyl ether (2×50 mL). The combined organic layers were washed with brine (100 mL), dried over MgSO4, filtered, and concentrated to afford a 1-allylcyclohexanol as a colorless oil (6.97, 103%) that contained a small amount of diethyl ether.

1. customThe reaction was quenched with saturated aqueous NH4Cl (100 mL)
2. additiondiluted with water (20 mL) and diethyl ether (50 mL)
3. customThe mixture was transferred to a separatory funnel
4. customthe layers were separated
5. extractionThe aqueous layer was extracted with diethyl ether (2×50 mL)
6. washThe combined organic layers were washed with brine (100 mL)
7. dry with materialdried over MgSO4
8. filtrationfiltered
9. concentrationconcentrated

ORD record

ord-fd795ecfc4a648c38822cae821933e84

Source dataset

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08541438B2