2-Butenoic acid, cyclohexyl ester, (2E)- synthesis
- Product Name:2-Butenoic acid, cyclohexyl ester, (2E)-
- CAS Number:31416-78-1
- Molecular formula:C10H16O2
- Molecular Weight:168.23
Yield:31416-78-1 85%
Reaction Conditions:
with toluene-4-sulfonic acid in toluene; for 18 h;Dean-Stark;Reflux;
Steps:
1 Preparation 1 : synthesis of (1 a) (2E)-2-butenoic acid, cyclohexyl ester (1 a).
In a fume hood, cyclohexanol (30 milliliters (ml_), 283.9 millimoles (mmol)), crotonic acid (25.9 g, 300.98 mmol), p-toluene sulfonic acid (1 .08 g, 5.68 mmol), and 40 ml. of toluene were charged into a 250 ml. round bottom flask. The flask was equipped with a Dean-Stark trap and a reflux condenser. The resulting reaction mixture was heated to reflux, and water that was generated was removed azeotropically. After refluxing for 18 hours, the reaction mixture was cooled to ambient temperature, and quenched with water (55 ml_). The resulting organic layer was separated and washed with saturated aqueous NaHC03 (2 x 40 ml_), then brine (30 ml_), and then dried over magnesium sulfate and filtered. The solvent was removed under reduced pressure to give compound (1 a) as a light yellow liquid (40.6 g) in 85% yield. 1 HNMR (400 MHz, Chloroform-d) d 6.93 (dq, 1 H), 5.81 (dq, 1 H), 4.84 - 4.73 (m, 1 H), 1 .92 - 1 .80 (m, 4H), 1 .77 - 1 .64 (m, 3H), 1 .59 - 1 .12 (m, 6H) and GC/MS (El) (Mass found = 168, 87, 69) were consistent with (2E)-2-butenoic acid, cyclohexyl ester.
References:
WO2020/68420,2020,A1 Location in patent:Paragraph 0056
107-93-7
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