Acetic Acid → Ethyl 3-methylpent-4-enoate

Temperature

100 °C

A stirred mixture of 36.06 g of crotyl alcohol, 162.2 g of triethyl orthoacetate and 2.22 g of propionic acid was slowly heated to 100° C. (1.25 hours), stirred and heated at 100°-115° C. for 1 hour, at 115°-145° C. for 2.5 hours, then at 145°-155° C. for 6 hours. The mixture was cooled in an ice bath and treated with 50 ml of glacial acetic acid and 50 ml of water. The mixture was stirred at room temperature for 45 minutes, diluted with ether, extracted with saturated sodium bicarbonate solution, then with brine and dried (MgSO4). The solvent was evaporated under reduced pressure and the residue was distilled under reduced pressure to give ethyl 3-methyl-4-pentenoate (3A), as a colorless liquid, b.p.: 88°-91° C. (60 Torr.).

1. temperatureheated at 100°-115° C. for 1 hour, at 115°-145° C. for 2.5 hours
2. temperatureThe mixture was cooled in an ice bath
3. stirringThe mixture was stirred at room temperature for 45 minutes
4. extractionextracted with saturated sodium bicarbonate solution
5. dry with materialwith brine and dried (MgSO4)
6. customThe solvent was evaporated under reduced pressure
7. distillationthe residue was distilled under reduced pressure

ORD record

ord-6dda0d16ea4b430cb5b81c4f833711f2

Source dataset

uspto-grants-1985_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04560401