4-Tert-butylcyclohexane-1-carboxylic acid → 4-tert-Butylcyclohexylmethanol

Temperature

0 °C

To a solution of 4-tert-butylcyclohexane carboxylic acid (10.0 g, 54.3 mmol of a mixture of cis and trans isomers) in anhydrous THF (distilled over Na/benzophenone) (44 mL) at 0° C., under argon were added dropwise B2H6 in THF (66.5 mL of 0.98M, 65.2 mmol). The reaction mixture was stirred at 0° C. for 2 hrs and then placed in the freezer overnight. The reaction was quenched by addition of saturated NaCl solution (50 mL) and was concentrated. The aqueous residue was extracted with EtOAc (3×200 mL) and the combined organic extracts were washed with sat. NaHCO3 solution (250 mL), followed by saturated brine (250 mL), dried over Na2SO4, and filtered. Concentration to dryness yielded 9.96 g of crude product which was purified via flash chromatography eluting with 25% EtOAc in hexane to yield an amorphous 4-(1,1-dimethylethyl)cyclohexanemethanol (9.18 g, 53.9 mmol) as a mixture of cis and trans isomers in 99% yield.

1. customplaced in the freezer overnight
2. customThe reaction was quenched by addition of saturated NaCl solution (50 mL)
3. concentrationwas concentrated
4. extractionThe aqueous residue was extracted with EtOAc (3×200 mL)
5. washthe combined organic extracts were washed with sat. NaHCO3 solution (250 mL)
6. dry with materialdried over Na2SO4
7. filtrationfiltered
8. concentrationConcentration to dryness
9. customyielded 9.96 g of crude product which
10. customwas purified via flash chromatography
11. washeluting with 25% EtOAc in hexane

ORD record

ord-1456051eead44124bf6a1130c7f4f683

Source dataset

uspto-grants-1992_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05128448