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

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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.

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