4-Hydroxy-4-methylcyclohexanone → 1-methylcyclohexane-1,4-diol

To a cooled (0° C.) solution of 4-hydroxy-4-methylcyclohexanone (1 equiv) in methanol (0.5 M) was added sodium borohydride (2 equiv).The resulting mixture was stirred at room temperature overnight. After the reaction was complete, the resulting mixture was quenched with water and extracted with ethyl acetate. The organic layers were combined, washed with brine (20 mL), dried over sodium sulfate, filtered and concentrated. The crude product was purified by silica gel flash column chromatography (0-10% DCM in methanol) to afford the title compound as a white solid (87% yield, cis/trans mixture). 1H NMR (300 MHz, DMSO-d6) δ ppm 4.34-4.32 (d, J=4.5 Hz, 1H), 4.29-4.27 (d, J=3.6 Hz, 0.45H), 4.12-4.06 (m, 0.47H), 4.00 (s, 0.39H), 3.97 (s, 1H), 3.82 (s, 0.48H), 3.55-3.50 (m, 0.47H), 3.20-3.17 (d, J=7.5 Hz, 1H), 1.76-1.62 (m, 1H), 1.60-1.40 (m, 8H), 1.35-1.20 (m, 4H), 1.07 (s, 1.5H), 1.05 (s, 3H).

1. customresulting mixture
2. customthe resulting mixture was quenched with water
3. extractionextracted with ethyl acetate
4. washwashed with brine (20 mL)
5. dry with materialdried over sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated
8. customThe crude product was purified by silica gel flash column chromatography (0-10% DCM in methanol)

ORD record

ord-5bec0da191ac413ab50d5535cb63d10d

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09346812B2