Methyl iodide → 3-(3-Methoxy-3-methylbutyl)-1,5-dimethylcyclohexan-1-ol

Participants

Reaction Steps

3-(3-Methoxy-3-methylbut-1-yl)-5-methylcyclohexan-1-one 5.0 gm 0.025 mol) dissolved in diethyl ether (5.0 mL) was added to a cooled (5~C.) solution of methylmagensium iodide formed by treating magnesium turnings (0.70 g, 0.028 mol) in diethyl ether (20 mL) with iodomethane (1.6 mL, 0.026 mol). After stirring 16 hours at 25~C., a saturated aqueous ammonium chloride solution (ca. 2 mL) was added and subsequent workup yielded 3-(3-methoxy-3-methylbutyl)-1,5-dimethylcyclohexan-1-ol as a mixture of diastereoisomers in a ratio of 2.9:65.6:1.9:29.6, bp0.5 147-149~C. This compound was determined to possess a warm woody note. NMR(CDCl3)δ 0.5(m,1H), 0.9(d,3H), 1.0-1.1(m,1H), 1.2(s,6H), 1.3(s,3H), 1.3-1.9(m,10H), 1.9-2.0(brs,1H), 3.2(s,3H); IR(neat) 3400, 2925, 1460, 1370, 1220, 1080 cm- 1 ; MS(m/e) 43, 55, 73, 107, 122, 163, 181, 213, 214.

Provenance & Evidence