(1R,2R,5R)-5-methyl-2-propan-2-ylcyclohexan-1-ol

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 100 ml capacity autoclave was charged with 3.1 g (20 mmol) of pulegol, 6.2 mg (0.01 mmol) of Ru(OAc)2(dppe) and methanol (3 ml), and the mixture was stirred at 50° C. for 18 hours while forcing 3 Mpa of hydrogen. After completion of the reaction, the reaction solution was cooled to room temperature and concentrated. A 3.1 g portion of a mixture of menthol:neomenthol:neoisomenthol=96:1.7:2.3 was obtained. The yield was 95.5%. After completion of the reaction the reaction solution was cooled to room temperature concentrated A 3.1 g portion of a mixture of menthol

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 100 ml capacity autoclave was charged with 1.0 g (6.5 mmol) of pulegol, 5% Pd-carbon (20 mg) and ethyl acetate (5 ml), and the mixture was stirred at 60° C. for 5 hours under a hydrogen pressure of 2 Mpa. After completion of the reaction, the reaction solution was cooled to room temperature and concentrated. A 0.99 g portion of a mixture of menthol:neoisomenthol=91:9 was obtained. The yield was 90%. After completion of the reaction the reaction solution was cooled to room temperature concentrated A 0.99 g portion of a mixture of menthol