Benzaldehyde → HCID 70102567, compound

HRID 1067303Notes

Reaction equation

HRID 1067303 reaction equation
C[C:2](C)([O-:4])C.[K+].[CH:7](=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[C:15]([O:23][CH3:24])(=[O:22])[CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19].[C:25](O)(C)(C)C>>[CH3:25][O:4][CH2:2][CH2:21][O:20][C:18](=[O:19])[CH2:17]/[C:16](/[C:15]([O:23][CH3:24])=[O:22])=[CH:7]\[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 4

HCID 240BenzaldehydeHCID 6386tert-Butanol2×HCID 7820Dimethyl SuccinateHCID 23665647Potassium tert-butoxide

Product 1

HCID 70102567HCID 70102567, compoundYield 65%

Procedure

To a solution of potassium tert-butoxide (16.8 g) in tert-butyl alcohol (150 ml) is added dropwise with stirring a solution of benzaldehyde (15.9 g) and dimethyl succinate (26.3 g) in tert-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 extracted with ethyl acetate. The extract is washed, dried, and concentrated under reduced pressure. The residue is dissolved in a mixture of toluene (50 ml) and ethylene glycol monomethyl ether (50 ml), and thereto is added dropwise thionyl chloride (16.4 ml) at 0° C. The mixture is allowed to stand at room temperature overnight, and the mixture is concentrated under reduced pressure. The residue is purified by silica gel column chromatography (eluent; hexane: ethyl acetate=4:1) to give (E)-3-methoxycarbonyl-4-phenyl-3-butenoic acid 2-methoxyethyl ester (26.9 g).

Workup

  1. extractionthe mixture is extracted with isopropyl ether
  2. extractionextracted with ethyl acetate
  3. washThe extract is washed
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe residue is dissolved in a mixture of toluene (50 ml) and ethylene glycol monomethyl ether (50 ml)
  7. additionis added dropwise thionyl chloride (16.4 ml) at 0° C
  8. waitto stand at room temperature overnight
  9. concentrationthe mixture is concentrated under reduced pressure
  10. customThe residue is purified by silica gel column chromatography (eluent; hexane: ethyl acetate=4:1)

Sources & evidence

ORD record
ord-0b7a8849328b48169db08e0ee3badb3e
Source dataset
uspto-grants-2001_06
Patent number
US06248743B1

Reaction notes

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