Trimethyl orthoformate → Methyl (E)-4-Chloro-3-methoxy-2-butenoate

Temperatur

150 °C

31.0 g (0.2 mol) of 4-chloro aceto acetic acid methyl ester was mixed with 106.0 g (1.0 mol) of orthoformic acid trimethyl ester. 30.0 g of Amberlyst-15 ion exchange resin was added under argon with stirring. The reaction temperature rose to 40° C. with vigorous development of gas. After 5 hours of stirring, no educt could any longer be detected by thin-layer chromatography. The ion exchange resin was filtered off, and the residue was distilled in a water jet vacuum. The distillate was mixed with 1.0 g of p-toluenesulfonic acid monohydrate and slowly heated to 150° C., whereby methanol distilled off. The reaction mass was then distilled in a water jet vacuum. 24.7 g of a colorless liquid with a boiling point bp12 =93° C. was obtained.

1. addition30.0 g of Amberlyst-15 ion exchange resin was added under argon
2. customrose to 40° C. with vigorous development of gas
3. stirringAfter 5 hours of stirring
4. filtrationThe ion exchange resin was filtered off
5. distillationthe residue was distilled in a water jet vacuum
6. additionThe distillate was mixed with 1.0 g of p-toluenesulfonic acid monohydrate
7. distillationwhereby methanol distilled off
8. distillationThe reaction mass was then distilled in a water jet vacuum

ORD-Eintrag

ord-bbb113d490c44f34bd0fc9d8e9eda19b

Quelldatensatz

uspto-grants-1988_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US04780545