Acetic Anhydride → Ethyl 3-ethoxy-2-(2,3,4,5-tetrafluorobenzoyl)acrylate

HRID 845025Notes

Reaction equation

HRID 845025 reaction equation
[F:1][C:2]1[C:15]([F:16])=[C:14]([F:17])[C:13]([F:18])=[CH:12][C:3]=1[C:4]([CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:5].[CH:19]([O-])([O-])[O:20][CH2:21][CH3:22].C(OC(=O)C)(=O)C>>[F:1][C:2]1[C:15]([F:16])=[C:14]([F:17])[C:13]([F:18])=[CH:12][C:3]=1[C:4]([C:6](=[CH:19][O:20][CH2:21][CH3:22])[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:5]

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 600916Ethyl 3-oxo-(2,3,4,5-tetrafluorophenyl)propanoateHCID 53630039Ethylorthoformate

Product 1

HCID 54346083Ethyl 3-ethoxy-2-(2,3,4,5-tetrafluorobenzoyl)acrylateYield 94.3%

Conditions

Temperature
150 °C

Procedure

A mixture of ethyl α-(2,3,4,5-tetrafluorobenzoyl)acetate (0.7 g), ethyl orthoformate (0.67 g) and acetic anhydride (0.74 g) is heated at 150° C. for 1.5 hour. After the reaction, the volatile material is distilled off at 120° C. under reduced pressure with a water pump to give ethyl 2-(2,3,4,5-tetrafluorobenzoyl)-3-ethoxyacrylate (0.8 g) as a mixture of cis and trans isomers.

Workup

  1. customAfter the reaction
  2. distillationthe volatile material is distilled off at 120° C. under reduced pressure with a water pump

Sources & evidence

ORD record
ord-fbe29bd3fc2c44abb97dd4a511f57025
Source dataset
uspto-grants-1988_07
Patent number
US04755513

Reaction notes

Loading…