Ethyl Bromide → cis-4-(1,1-Dimethylethyl)-alpha-ethylcyclohexanemethanol

To a mixture of 24 g (1.0 mol) magnesium turnings and 100 ml anhydrous ethyl ether was added 109 g (1.0 mol) bromoethane. The resulting solution was heated under reflux for two hours. To the above solution, 109 g (0.9 mol) 1-formyl-4-t-butylcyclohexane was added dropwise over 1 hour. After addition, the mixture was heated under reflux for four hours, allowed to cool, and then added to 100 ml of a mixture of saturated ammonium chloride solution and ice. The mixture was extracted with ether (3×100 ml) and the extract washed with water, dried, concentrated, and distilled to give a 1:1 mixture of cis and trans-1-(1-hydroxypropyl)-4-t-butylcyclohexane: 116 g (66% yield); bp 89-95 (1 mm); mol wt 198 (ms); nmr 0.85 (12 H, s, methyl H), 3.1-3.9 (1H, broad, αH); ir, 3350, 1364, 970.

1. temperatureThe resulting solution was heated
2. temperatureunder reflux for two hours
3. additionAfter addition
4. temperaturethe mixture was heated
5. temperatureunder reflux for four hours
6. temperatureto cool
7. extractionThe mixture was extracted with ether (3×100 ml)
8. washthe extract washed with water
9. customdried
10. concentrationconcentrated
11. distillationdistilled
12. customto give

ORD record

ord-c8d1154ce05643f285f495022709c585

Source dataset

uspto-grants-1980_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04181631