5-methyl-2-propan-2-ylidenecyclohexan-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

Conditions: temp:30.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 200 ml capacity autoclave was charged with 30.4 g (200 mmol) of pulegone, 19.1 mg (0.02 mmol) of RuCl2(PPh3)3(propanediamine), 44.9 mg (0.4 mmol) of t-BuOK and 2-propanol (15 ml), and the mixture was stirred at 30° C. for 18 hours while forcing 3 Mpa of hydrogen. After completion of the reaction, hydrogen was purged and the reaction solution was concentrated and distilled under a reduced pressure to obtain 30.2 g of pulegol. The yield was 98%. was purged the reaction solution was concentrated distilled under a reduced pressure

Conditions: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 100 ml capacity autoclave was charged with 3.04 g (20 mmol) of pulegone, 19.1 mg (0.02 mmol) of RuCl2(PPh3)3, 0.2 M 1,3-diaminopropane 2-propanol solution (0.2 ml), 0.2 M potassium hydroxide 2-propanol solution (1.0 ml) and 2-propanol (14 ml), and the mixture was stirred at 25° C. for 3 hours under a hydrogen pressure of 2 MPa. After completion of the reaction, hydrogen was purged, the reaction solution was concentrated and then distillation was carried out under a reduced pressure to obtain 2.61 g of pulegol. The yield was 85%. was purged the reaction solution was concentrated distillation

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

Procedure: A 500 ml capacity autoclave was charged with 150 g (1 mol) of piperitenone, 18.6 mg (0.04 mmol) of [Rh(cod)2]PF6, 47.2 mg (0.04 mmol) of (S)-DTBM-SEGPHOS, 14.8 mg (0.02 mmol) of BrPPh3(CH2)4PPh3Br and 7.5 ml of ethyl acetate, and the reaction was carried out at 50° C. for 20 hours under a hydrogen pressure of 3 Mpa. After completion of the reaction, hydrogen was purged, the reaction solution was concentrated and then distillation was carried out under a reduced pressure to obtain 136.8 g of pulegol. The yield was 90%. was purged the reaction solution was concentrated distillation