Water → 2-(4-Methylcyclohex-3-en-1-yl)propane-2-thiol

Participants

Reaction Conditions

Reaction Steps

0.637 g (3.8 mM) of the compound prepared according to letter (b) above in 12 ml of tetrahydrofuran (THF) were added under nitrogen atmosphere to a stirred boiling suspension of 72 mg (1.9 mM) of LiAlH4 in 3 ml of THF. The reaction mixture was refluxed for 1 further hour, then cooled at 0° C. and the excess of LiAlH4 decomposed by addition of water. The obtained mixture was then extracted with ether (3×) and the organic phase washed with water (3×), dried and evaporated. After fractional distillation of the crude residue, there were obtained 0.450 g (69% yield) of the desired 1-p-menthene-8-thiol, b.p. 40° C./0.133 Pa.

Provenance & Evidence