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 1M 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 was 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%). Step 2. 1-Methylcyclohexylcarboxaldehyde:

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 was washed with water and saturated sodium chloride
8. customdried
9. filtrationfiltered
10. concentrationconcentrated
11. customThe residue was purified by flash chromatography

ORD record

ord-f5b2fb755d9c41b395f9cddf1c47d0a7

Source dataset

uspto-grants-2006_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07012066B2