2-Cyclohexen-1-one, 4,4-dimethyl- → 2-Cyclohexen-1-ol, 4,4-dimethyl-

Sodium borohydride (5.03 g, 133 mmol) was added portion-wise to a stirred solution of 4,4-dimethylcyclohex-2-enone (15.0 g, 121 mmol) in methanol (403 mL) in a water bath. Once addition was complete, the solution was allowed to stir under a nitrogen atmosphere at room temperature for 3 h. The reaction mixture was diluted with water (150 mL) and the majority of the methanol was removed under reduced pressure. The aqueous layer was extracted with ethyl acetate (2×200 mL). The combine ethyl acetate extracts were dried over anhydrous magnesium sulfate, filtered, and concentrated to an oil under reduced pressure to afford 4,4-dimethylcyclohex-2-enol (13.4 g, 106 mmol, 88% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 5.41-5.57 (m, 1H), 5.24-5.42 (m, 1H), 4.61 (d, J=5.47 Hz, 1H), 3.82-3.99 (m, 1H), 1.65-1.83 (m, 1H), 1.21-1.59 (m, 3H), 0.93 (d, J=15.23 Hz, 6H).

1. additionOnce addition
2. customthe majority of the methanol was removed under reduced pressure
3. extractionThe aqueous layer was extracted with ethyl acetate (2×200 mL)
4. dry with materialThe combine ethyl acetate extracts were dried over anhydrous magnesium sulfate
5. filtrationfiltered
6. concentrationconcentrated to an oil under reduced pressure

ORD record

ord-411a96bf55fe497b9a54a3e013877f6f

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09139534B2