Hydrochloric Acid → (4-Cyclohexylphenyl)methanol

Under a nitrogen stream, tetrahydrofuran (1.2 L, 15.0 v/w) was added to 4-cyclohexylbenzoic acid (80.0 g, 0.382 mol) and then isobutyl chlorocarbonate (52.0 ml, 0.401 mol) was added. Triethylamine (56.0 ml, 0.401 mol) was added to the reaction mixture with stirring under ice-cooling and the mixture was stirred at the same temperature for 30 min. The resulting precipitate was collected by filtration. To a suspension of sodium borohydride (58.0 g, 1.53 mol) in tetrahydrofuran (160 ml, 2.0 v/w) prepared in a different reaction vessel was carefully added the above-mentioned filtrate with stirring under ice-cooling under a nitrogen stream. After stirring at room temperature for 1.5 hr, distilled water (160 ml, 2.0 v/w) was added with stirring under ice-cooling. After stirring under ice-cooling for 20 min, 2N-hydrochloric acid (825 ml, 4.3 eq) was added. After stirring at room temperature for 30 min, the mixture was extracted with ethyl acetate (400 ml) and the organic layer was washed successively with distilled water (100 ml), 2N-aqueous sodium hydroxide solution (100 ml), distilled water (100 ml) and saturated brine (100 ml), and dried over magnesium sulfate (70 g). After filtration and solvent evaporation, the residue was dried in vacuo to give the title compound (63.8 g, yield 87.8%) as a white solid.

1. temperaturecooling
2. stirringthe mixture was stirred at the same temperature for 30 min
3. filtrationThe resulting precipitate was collected by filtration
4. customprepared in a different reaction vessel
5. additionwas carefully added the above-mentioned filtrate
6. stirringwith stirring under ice-
7. temperaturecooling under a nitrogen stream
8. stirringAfter stirring at room temperature for 1.5 hr
9. distillationdistilled water (160 ml, 2.0 v/w)
10. additionwas added
11. stirringwith stirring under ice-
12. temperaturecooling
13. stirringAfter stirring under ice-
14. temperaturecooling for 20 min
15. stirringAfter stirring at room temperature for 30 min
16. extractionthe mixture was extracted with ethyl acetate (400 ml)
17. washthe organic layer was washed successively with distilled water (100 ml), 2N-aqueous sodium hydroxide solution (100 ml)
18. distillationdistilled water (100 ml) and saturated brine (100 ml)
19. dry with materialdried over magnesium sulfate (70 g)
20. filtrationAfter filtration and solvent evaporation
21. customthe residue was dried in vacuo

ORD record

ord-6e8fc2c037c14e4ea09952b06b9ffdf9

Source dataset

uspto-grants-2007_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07163952B2