Novel aldehydes and nitriles from isophorone, and the use thereof in perfumery
A technology of uses and groups, applied in the field of new aldehydes and nitriles, can solve problems such as olfactory performance reports
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Embodiment 1
[0120] Embodiment 1: 2-(2,4,4-trimethyl-1-cyclopentene) acetonitrile (1) and 2-(3,3,5-trimethyl-1-cyclopentene) acetonitrile (2 ) preparation
[0121] In a round bottom flask, cyclopentanone A, 1.5 equivalents of methyl cyanoacetate, 1 equivalent of acetic acid, and 10 mol% ammonium acetate were dissolved in cyclohexane. The water formed is removed by refluxing the reaction medium using an apparatus of the Dean-Stark type. After refluxing overnight, A was fully converted (>90%), at which point the reaction medium was allowed to return to ambient temperature. Washing with sodium bicarbonate solution followed by aqueous sodium chloride solution. After drying over magnesium sulfate, filtering through filter paper and evaporating the solvent, the crude product B was rectified under reduced pressure.
[0122] Boiling point = 80°C / 0.3 Torr
[0123] In a round bottom flask, methyl 2-cyano-2-(2,4,4-trimethylcyclopentylene)acetate B was dissolved in 98:2 NMP ( N-methylpyrrolidone)...
Embodiment 2
[0135] Embodiment 2: the preparation of 2-(2,4,4-trimethylcyclopentene) acetonitrile (3)
[0136] Under an inert atmosphere, 1.1 equivalents of diethylphosphonoacetonitrile was dissolved in THF (tetrahydrofuran). At about 10° C., 1.1 equivalents of a solution of butyllithium in hexane was added dropwise thereto. The mixture was then stirred at ambient temperature for 1 hour, followed by the dropwise addition of 1 equivalent of cyclopentanone A at about 10°C. The reaction medium is stirred for several hours at ambient temperature and subsequently poured into a 10% HCl solution. The aqueous phase was extracted 3 times with MTBE. The combined organic phases are washed with sodium bicarbonate solution and subsequently with aqueous sodium chloride. After drying over magnesium sulfate, filtering through filter paper and evaporating the solvent, the crude product was distilled under reduced pressure. A 75:25 mixture of trans and cis isomers of 2-(2,4,4-trimethylcyclopentylene)ace...
Embodiment 3
[0148] Embodiment 3: the preparation of 2-(2,4,4-trimethylcyclopentylene) acetonitrile (4)
[0149] A solution in toluene containing 1 equivalent of the mixture of compound 1 and compound 2 obtained in Example 1 and 5% by weight of activated carbon loaded with 5% palladium was placed in 20 bar of hydrogen at 40 °C on In a high pressure reactor. At the end of the reaction, the autoclave was purged with nitrogen and the solution was filtered through celite. The filtrate was concentrated. The crude product was purified by distillation and was obtained as two diastereomers in a ratio of 70:30.
[0150] Boiling point = 80°C / 6 Torr
[0151] Olfactory description: Fresh, fresh, zesty, intense.
[0152] Major isomers:
[0153] 1 H NMR (200 MHz, CDCl 3 ): δ (ppm) 0.92-1.08 (m, 3H), 1.04 (s, 6H), 1.15-1.42 (m, 2H), 1.60-1.87 (m, 3H), 2.23-2.44 (m, 3H).
[0154] 13 C NMR (50 MHz, CDCl 3 ): δ (ppm) 18.82, 21.33, 31.54, 37.09, 39.94, 43.66, 47.86, 50.59, 119.42.
[0155] MS[e / m(...
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