4-Bromotoluene → 2-(4-Methylphenyl)cyclohexan-1-ol

Temperature

-20 °C

A solution of p-tolyl-magnesium bromide, prepared from 17.1 g (100 mmol) p-tolyl bromide and 2.43 g (100 mmol) magnesium, in 100 ml abs. tetrahydrofuran was cooled to −20° C. and 1 g CuBr-dimethylsulfid complex was added and the mixture stirred at −20° C. for 10 min. To this a solution of 10 ml (9.80 g, 100 mmol) cyclohexene oxide in 10 ml abs. tetrahydrofuran was added drop-wise and the reaction warmed to 0° C. at which an exothermic reaction starts. With cooling the temperature was maintained below 25° C. The reaction mixture was stirred at 0 to 5° C. for additional 2h, then quenched with saturated aqueous ammonium chloride solution and extracted with tert.-butyl methyl ether. The organic extract was washed with water, dried over Na2SO4, filtered and evaporated. The residue, 18.25 g slightly yellow crystals was re-crystallizes from n-hexane: 9.91 g rac-2-p-tolyl-cyclohexanol as colorless crystals: m.p. 72.5–73° C., MS (EI): 190.1 M+.

1. addition1 g CuBr-dimethylsulfid complex was added
2. temperaturethe reaction warmed to 0° C. at which
3. customan exothermic reaction
4. temperatureWith cooling the temperature
5. temperaturewas maintained below 25° C
6. customquenched with saturated aqueous ammonium chloride solution
7. extractionextracted with tert.-butyl methyl ether
8. extractionThe organic extract
9. washwas washed with water
10. dry with materialdried over Na2SO4
11. filtrationfiltered
12. customevaporated
13. customThe residue, 18.25 g slightly yellow crystals was re-crystallizes from n-hexane

ORD record

ord-aea8adb4ddad4f63befe4dbd63d14679

Source dataset

uspto-grants-2007_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07189850B2