76. Researches in the menthone series. Part XII. Isolation and characterisation of the neoisomenthols

The Stereoisomerism of Cyclohexane Derivatives.

“…Using the aluminum alkoxides of sterically hindered secondary alcohols, such as methyl-tert-butylcarbinol, even higher yields of neomenthol have been realized than those (70 per cent) obtained with aluminum isopropoxide. Similarly, isomenthol and neoisomenthol have been related to isomenthone (252,257). Elimination reactions of derivatives oj menthol and neomenthol {HI) The assignment of a trans (ee or pp) configuration to the methyl and isopropyl groups in menthol and neomenthol (on the basis of the relationship of these alcohols to menthone) leaves the orientation of the hydroxyl group still to be clarified.…”