Ethyl vinyl ether → HCID 54481174, compound

HRID 1090810Notes

Reaction equation

HRID 1090810 reaction equation
[CH:1]([O:3][CH2:4][CH3:5])=[CH2:2].Cl[C:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:8]>>[CH2:1]([O:3][CH:4]=[CH:5][C:7](=[O:8])[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH3:2]

Participants

3

Reactant 2

HCID 8023Ethyl vinyl etherHCID 20884Ethoxalyl chloride

Product 1

HCID 54481174HCID 54481174, compound

Procedure

145 g of ethyl vinyl ether were added dropwise to 137 g of ethyl chloroformylformate with cooling using ice/common salt; after warming to room temperature, the mixture was stirred for a further 20 hours. The volatile components were removed by distillation, and the residue was fractionated in a water-pump vacuum. Ethyl 4-ethoxy-2-oxobut-3-enoate of boiling point 140°-143° C./13 torr were obtained. 17.5 g of product were dissolved in 200 ml of toluene. 17.5 g of 2,6-dichlorophenylhydrazine were added at 0° C. with stirring. The mixture was slowly heated to boiling, and ethanol and water were removed in a water separator until the boiling point remained constant at 111° C. The residue was diluted with toluene, washed twice with 2N hydrochloric acid, saturated hydrogen carbonate solution and water, dried, evaporated to dryness and recrystallized from ethanol.

Workup

  1. temperaturewith cooling
  2. customThe volatile components were removed by distillation

Sources & evidence

ORD record
ord-5872ae775d7649ee82102e25fd546855
Source dataset
uspto-grants-1992_01
Patent number
US05082949

Reaction notes

Loading…