Cyclohexanone, 2-methyl-5-(1-methylethyl)-, (5S)- (9CI) synthesis
- Product Name:Cyclohexanone, 2-methyl-5-(1-methylethyl)-, (5S)- (9CI)
- CAS Number:160168-89-8
- Molecular formula:C10H18O
- Molecular Weight:154.25
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Yield:160168-89-8 99%
Reaction Conditions:
with Rh/Al2O3;hydrogen in ethanol at 20; under 31503.2 Torr; for 3.5 h;Autoclave;
Steps:
4.1.1.2. Catalytic hydrogenation catalyzed by Rh/Al2O3
A solution of carvone (13) (7.49 g, 50 mmol) in ethanol (55 mL) was hydrogenated in the presence of Rh/Al2O3 (0.203 g, 0.025 mmol) at 4.2 MPa in an autoclave at room temperature for 3.5 h. After filtration of the catalyst, evaporation of the solvent followed by Kugelrohr distillation gave tetrahydrocarvone (14) (7.60 g, 99%). [α]D21 -37.8 (c 1.32, CHCl3); IR (CHCl3) νmax/cm-1 3013, 2963, 1702, 1457, 1369, 1315; 1H NMR (400 MHz, CDCl3) δ (ppm) 2.48-2.31 (m, 2H), 2.09 (m, 1H), 1.87 (m, 1H), 1.72-1.25 (m, 4H), 1.29 (ddd, 1H, J 25.8, 12.8, 3.2 Hz), 1.09 (d, 1.5H, J 6.8 Hz), 1.01 (d, 1.5H, J 6.4 Hz), 0.90 (dd, 3H, J 6.8, 6.0 Hz), 0.89 (dd, 3H, J 6.4, 3.6 Hz); 13C NMR (100 MHz, CDCl3) δ (ppm) 214.3, 212.8, 46.2, 44.9, 44.5, 44.4, 43.9, 42.6, 34.7, 32.4, 31.0, 30.2, 28.5, 24.7, 19.7, 19.6, 19.2, 19.0, 15.4, 14.0; HRMS m/z calcd for C10H18O 154.1358, found 154.1359.
References:
Hagiwara, Hisahiro;Fukushima, Masakazu;Kinugawa, Kimihiko;Matsui, Takuya;Hoshi, Takashi;Suzuki, Toshio [Tetrahedron,2011,vol. 67,# 22,p. 4061 - 4068] Location in patent:experimental part
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![1,2-Cyclohexanediol, 1-methyl-4-(1-methylethyl)-, [1S-(1α,2β,4β)]- (9CI)](/CAS/20210305/GIF/5745-59-5.gif)
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