Cyclohexyl crotonate synthesis
- Product Name:Cyclohexyl crotonate
- CAS Number:16491-62-6
- Molecular formula:C10H16O2
- Molecular Weight:168.23
Yield: 290 g
Reaction Conditions:
with toluene-4-sulfonic acid in toluene at 120 - 130;Dean-Stark;
Steps:
XII Preparation of But-2-enoic acid cyclohexyl ester (Structure XII)
EXAMPLE XII
Preparation of But-2-enoic acid cyclohexyl ester (Structure XII)
Cyclohexanol (220 g), crotonic acid (199 g), PTSA (8 g), and toluene (300 mL) were charged into a 2-L reaction flask fitted with a mechanical stirrer, a thermocouple, a Dean-Stark trap, and a condenser.
The reaction mixture was heated to reflux at about 120-130° C. Water was removed azeotropically.
The reaction was aged at reflux for about 4-5 hours until no more water evolved.
The reaction mixture was cooled to room temperature and quenched with water (400 mL).
The organic layer was separated and subsequently washed with sodium carbonate (5%, 300 mL), and further fractional distilled to provide but-2-enoic acid cyclohexyl ester (290 g) with a boiling point of 104° C. at 13 mmHg.
1H NMR (CDCl3, 500 MHz): 6.95 ppm (d, 1H, J=15.45 Hz, of q, J=6.92 Hz), 5.83 ppm (d, 1H, J=15.45 Hz, of q, J=1.48 Hz), 4.77-4.88 ppm (m, 1H), 1.87 ppm (d, 3H, J=6.92 Hz, of d, J=1.48 Hz), 1.20-1.92 ppm (m, 10H)
References:
International Flavors & Fragrances Inc.;Narula, Anubhav P. S.;Weiss, Richard A.;Lasome, James Anthony US8785677, 2014, B1 Location in patent:Page/Page column 16; 17
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