L-MENTHONE synthesis
- Product Name:L-MENTHONE
- CAS Number:14073-97-3
- Molecular formula:C10H18O
- Molecular Weight:154.25
2) Selective hydrogenation: D-Pulegone is hydrogenated at 70°C under 100 atm H? pressure for 23 h in the presence of the catalyst. After removing solvents, levomenthol is obtained by
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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
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