Potassium Carbonate → 2-Butenoic acid, 4,4-dimethoxy-3-methyl-, ethyl ester

HRID 1110420Notes

Reaction equation

HRID 1110420 reaction equation
[CH3:1][O:2][CH:3]([O:7][CH3:8])[C:4]([CH3:6])=O.C(OP([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])(OCC)=O)C.C(=O)([O-])[O-].[K+].[K+]>O>[CH3:1][O:2][CH:3]([O:7][CH3:8])[C:4]([CH3:6])=[CH:17][C:18]([O:20][CH2:21][CH3:22])=[O:19]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 13345Triethyl phosphonoacetateHCID 80650Pyruvic aldehyde dimethyl acetal

Product 1

HCID 30193392-Butenoic acid, 4,4-dimethoxy-3-methyl-, ethyl ester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 50 mmol of 1,1-dimethoxyacetone and 60 mmol of ethyl 2-(diethoxyphosphoryl)acetate is added in the course of 1 hour to a suspension of 125 mmol of potassium carbonate in 10 ml of water with vigorous stirring and with temperature maintained at between 20° and 30° C. When the addition is complete, stirring is continued for 24 hours at room temperature and the insoluble matter is then removed by filtration and washed with diethyl ether. The organic phase is separated and washed with saturated sodium chloride solution to neutrality. After drying and evaporation of the solvent, the product is purified by distillation under vacuum, which yields an (E+Z) isomer mixture in the form of an oil.

Workup

  1. temperaturemaintained at between 20° and 30° C
  2. additionWhen the addition
  3. stirringstirring
  4. customthe insoluble matter is then removed by filtration
  5. washwashed with diethyl ether
  6. customThe organic phase is separated
  7. washwashed with saturated sodium chloride solution to neutrality
  8. customAfter drying
  9. customevaporation of the solvent
  10. distillationthe product is purified by distillation under vacuum, which
  11. customyields an (E+Z) isomer mixture in the form of an oil

Sources & evidence

ORD record
ord-ef40f8ee53914eb1a925e07a6dc39140
Source dataset
uspto-grants-1990_12
Patent number
US04975454

Reaction notes

Loading…