4-acetyl-1-methyl-1-cyclohexene manufacturers
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| | 4-acetyl-1-methyl-1-cyclohexene Basic information |
| Product Name: | 4-acetyl-1-methyl-1-cyclohexene | | Synonyms: | 4-acetyl-1-methyl-1-cyclohexene;1-Methyl-1-cyclohexene-4-yl(methyl) ketone;1-Methyl-4-acetylcyclohexene;4'-Methyl-1',2',3',6'-tetrahydroacetophenone;Methyl(4-methyl-3-cyclohexenyl) ketone;4-Methyl-3-cyclohexen-1-yl methyl ketone;1-(4-Methylcyclohex-3-en-1-yl)ethanone;1-(4-methylcyclohex-3-en-1-yl)ethan-1-one | | CAS: | 6090-09-1 | | MF: | C9H14O | | MW: | 138.21 | | EINECS: | | | Product Categories: | | | Mol File: | 6090-09-1.mol |  |
| | 4-acetyl-1-methyl-1-cyclohexene Chemical Properties |
| | 4-acetyl-1-methyl-1-cyclohexene Usage And Synthesis |
| Uses | 1-(4-methyl-3-cyclohexen-1-yl)ethanone is an essential oil found in Cedrus atlantica wood and orange peels. | | Definition | ChEBI: 4-Acetyl-1-methylcyclohexene is a ketone. | | Synthesis | The general procedure for the synthesis of 4-acetyl-1-methyl-cyclohexene from the compound (CAS: 55511-67-6) was as follows: a crude mixture of 12 and 9 (1.48 g) was dissolved in dichloromethane (8 mL) at 0°C and added slowly and dropwise to a pre-prepared dichloromethane (2.69 g, 7.77 mmol) and diatomaceous earth (2.67 g) (40 mL) suspension. After dropwise addition, the reaction mixture was stirred at room temperature for 2 hours. Upon completion of the reaction, it was filtered through a short diatomaceous earth pad and silica gel column and rinsed with dichloromethane. After evaporation to remove the solvent, the crude product was further purified by silica gel column chromatography using petroleum ether/ethyl ether (8:2) as eluent, resulting in 410 mg of 9 as a light yellow oil. When purified 12 (543 mg, 3.9 mmol) was used as starting material, the same experimental protocol was employed to obtain 500 mg (93% yield) of the target product. The structure of the product was confirmed by the following characterization data: 1H NMR (400 MHz, CDCl3): δ5.31 (s, 1H), 2.50-2.39 (m, 1H), 2.16-1.84 (m, 6H), 2.10 (s, 3H), 1.58 (s, 3H). 13C NMR (100 MHz, CDCl3): δ211.99 ,133.77, 119.23, 47.20, 29.46, 27.92, 27.02, 24.87, 23.36. MS (EI, 70eV, m/z %): 43 (32), 67 (36), 77 (17), 79 (26), 93 (18), 95 (78), 105 (17), 123 (50), 138 ( M+, 100). | | Purification Methods | Purify it by fractionation under reduced pressure in vacuo, and if it is almost pure it can be fractionated at atmospheric pressure, preferably in an inert atmosphere. It forms two semicarbazones one of which is more soluble in *C6H6, and both can be recrystallised from EtOH; the more soluble has m 149o(151o), and the less soluble has m 172-175o(191o). The 4-nitrophenylhydrazone has m 166-167o and the 2,4-dinitrophenylhydrazone has m 114-115o. [Pfau & Plattner Helv Chim Acta 17 129, 142 1934, Adler & Vogt Justus Liebigs Ann Chem 564 109 1949.] | | References | [1] Phytochemistry, 2017, vol. 144, p. 208 - 215 |
| | 4-acetyl-1-methyl-1-cyclohexene Preparation Products And Raw materials |
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