Benzaldehyde → (E)-3-methoxycarbonyl-4-phenyl-3-butenoic acid methyl ester

HRID 439614Notes

Reaction equation

HRID 439614 reaction equation
CC(C)([O-])C.[K+].[CH:7](=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH3:15][O:16][C:17](=[O:24])[CH2:18][CH2:19][C:20]([O:22][CH3:23])=[O:21]>C(O)(C)(C)C>[CH3:15][O:16][C:17](=[O:24])[CH2:18]/[C:19](/[C:20]([O:22][CH3:23])=[O:21])=[CH:7]\[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 7820Dimethyl SuccinateHCID 23665647Potassium tert-butoxide

Product 1

HCID 6186590(E)-3-methoxycarbonyl-4-phenyl-3-butenoic acid methyl esterYield 66.1%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent2×

Procedure

To a solution of potassium t-butoxide (16.8 g) in t-butyl alcohol (150 ml) is added dropwise with stirring a solution of benzaldehyde (15.9 g) and succinic acid dimethyl ester (26.3 g) in t-butyl alcohol (20 ml) at room temperature, and the mixture is stirred for 30 minutes. The reaction mixture is poured into ice-water (200 ml), and the mixture is extracted with isopropyl ether. The pH value of the aqueous layer is adjusted to pH 2-3, and the mixture is extracted with ethyl acetate. The ethyl acetate layer is washed, dried, and evaporated to remove the solvent. The residue is dissolved in methanol (75 ml), and thereto is added dropwise thionyl chloride (10.9 ml) under ice-cooling. The mixture is allowed to stand at room temperature overnight, and then evaporated to remove the solvent. To the residue is added isopropyl ether, and the mixture is washed, dried, and evaporated to remove the solvent. The resulting residue is distilled under reduced pressure to give (E)-3-methoxycarbonyl-4-phenyl-3-butenoic acid methyl ester (23.2 g) as colorless oil.

Workup

  1. extractionthe mixture is extracted with isopropyl ether
  2. extractionthe mixture is extracted with ethyl acetate
  3. washThe ethyl acetate layer is washed
  4. customdried
  5. customevaporated
  6. customto remove the solvent
  7. dissolutionThe residue is dissolved in methanol (75 ml)
  8. additionis added dropwise thionyl chloride (10.9 ml) under ice-
  9. temperaturecooling
  10. waitto stand at room temperature overnight
  11. customevaporated
  12. customto remove the solvent
  13. additionTo the residue is added isopropyl ether
  14. washthe mixture is washed
  15. customdried
  16. customevaporated
  17. customto remove the solvent
  18. distillationThe resulting residue is distilled under reduced pressure

Sources & evidence

ORD record
ord-f8e6a35fff1d49518348a43bb22f4e2c
Source dataset
uspto-grants-1996_05
Patent number
US05514815

Reaction notes

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