ChemicalBook CAS DataBase List L-MENTHONE

L-MENTHONE synthesis

9synthesis methods

Product Name:L-MENTHONE
CAS Number:14073-97-3
Molecular formula:C10H18O
Molecular Weight:154.25

Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1R)-

904840-84-2
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14073-97-3
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Yield:14073-97-3 836 g

Reaction Conditions:

with Dess-Martin periodane in dichloromethane at 20; for 16 h;Inert atmosphere;

Steps:

Intermediate 1 : L-menthone

Three batches of the same reaction were carried out in parallel. To a solution of (R)-menthol (300g) in DCM (2.7M) was added Dess-martin reagent (1.1 Oeq) at 20°C under N2. The reaction was stirred at 20°C for 16 hrs. The three reactions were combined for workup. The resulting mixture was poured into water (4.3V). The aqueous phase was extracted with DCM (1.4V x 3). The combined organic phases were washed with a saturated aqueous solution of Na2SC>3 (1.4V x 2). The organic phase was checked by potassium iodidestarch test paper: the test paper did not change to blue. The organic phase was washed with brine (1.4V x 2), dried with anhydrous Na2SO4, filtered and concentrated under vacuum. The residue was purified by flash chromatography with petroleum ether & ethyl acetate to give L-menthone (836g) as colorless oil. 1H NMR: 400 MHz DMSO-cfe (8 ppm): 1.98-2.18 (m, 5H), 1.72-1.86 (m, 2H), 1.24-1.40 (m, 2H), 0.95 (d, J = 6.4 Hz, 3H), 0.85 (d, J = 6.8 Hz, 3H), 0.79 (d, J = 6.8 Hz, 3H).

References:

WO2022/133027,2022,A1 Location in patent:Page/Page column 65