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

To a cooled (0° C.) solution of 4-hydroxy-4-methylcyclohexanone (1 equiv) in MeOH (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 MeOH) 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. customthe resulting mixture was quenched with water
2. extractionextracted with ethyl acetate
3. washwashed with brine (20 mL)
4. dry with materialdried over sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated
7. customThe crude product was purified by silica gel flash column chromatography (0-10% DCM in MeOH)

ORD record

ord-cfe52e01b9004c588a97938d9eed9465

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09428509B2