Phosphoric Acid → Methyl 3,3-dimethyl-4-pentenoate

A mixture of trimethyl orthoacetate (120 g; 1 mole), 3-methylbut-2-enol (21.5 g; 0.25 mole) and orthophosphoric acid (1.5 g; 0.015 mole) was placed in a flask equipped with a stirrer and a 10 cm fractionating column packed with Fenske rings. The mixture was heated, with stirring, to a temperature of 95° to 110° C. and maintained at this temperature for a period of 2 hours while the methanol formed was collected by distillation. The excess trimethyl orthoacetate was distilled from the reaction mixture over a period of 1 hour during which time the temperature of the reaction mixture was raised to 140°-145° C. The reaction mixture was heated with stirring, at a temperature of 140°-145° C. for a period of 1 hour and then product was distilled to give methyl 3,3-dimethylpent-4-enoate (14.4 g; 40.6%); bp 95°-99° C. at 140 mm Hg.

1. customwas placed in a flask
2. customequipped with a stirrer
3. temperatureThe mixture was heated
4. customformed
5. distillationwas collected by distillation
6. distillationThe excess trimethyl orthoacetate was distilled from the reaction mixture over a period of 1 hour during which time the temperature of the reaction mixture
7. temperaturewas raised to 140°-145° C
8. temperatureThe reaction mixture was heated
9. stirringwith stirring, at a temperature of 140°-145° C. for a period of 1 hour
10. distillationproduct was distilled

ORD record

ord-91bbd67ab6fc4980aaa8921902aca425

Source dataset

uspto-grants-1983_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04374264