3-Hexen-1-ol → But-2-enoic acid hex-3-enyl ester

Temperature

125 °C

Hex-3-en-1-ol (179 g), crotonic acid (181 g), PTSA (7.2 g), and toluene (250 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 distilled to provide but-2-enoic acid hex-3-enyl ester (247 g) with a boiling point of 109° C. at 20 mmHg.

1. customfitted with a mechanical stirrer
2. temperatureThe reaction mixture was heated
3. customWater was removed azeotropically
4. temperatureat reflux for about 4-5 hours until no more water
5. temperatureThe reaction mixture was cooled to room temperature
6. customquenched with water (400 mL)
7. customThe organic layer was separated
8. washsubsequently washed with sodium carbonate (5%, 300 mL)
9. distillationfurther distilled

ORD record

ord-5e2798dfb17944cea50566fb0e9b83c0

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08772533B1