1-Methylcyclohexanecarboxylic acid → (1-Methylcyclohexyl)methanol

To a solution of 1-methyl-1-hydroxycarbonylcyclohexane (10 g, 70 mmol) in tetrahydrofuran (300 mL) at 0° C. was added 1 M diborane in tetrahydrofuran (200 mL, 200 mmol) over 90 minutes. The cooling bath was removed and the reaction mixture was stirred at room temperature for two days. The remaining borane was quenched by the slow addition of saturated sodium bisulfate (10 mL) over 90 min with cooling. Additional saturated sodium bisulfate (200 mL) was added and after 20 min of stirring the aqueous layer was removed. The organic layer washed with water and saturated sodium chloride, dried, filtered and concentrated. The residue was purified by flash chromatography using 20% diethylether in hexanes to give 1-methyl-1-hydroxymethylcyclohexane (6.17 g, 48 mmol, 69%).

1. customThe cooling bath was removed
2. customThe remaining borane was quenched by the slow addition of saturated sodium bisulfate (10 mL) over 90 min
3. temperaturewith cooling
4. additionAdditional saturated sodium bisulfate (200 mL) was added and after 20 min
5. stirringof stirring the aqueous layer
6. customwas removed
7. washThe organic layer washed with water and saturated sodium chloride
8. customdried
9. filtrationfiltered
10. concentrationconcentrated
11. customThe residue was purified by flash chromatography

ORD record

ord-5c333518877545a2b43586bc5ed8b2f5

Source dataset

uspto-grants-2009_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07592316B2