Sodium → HCID 54411654, compound

HRID 1680044Notes

Reaction equation

HRID 1680044 reaction equation
[Na].[CH2:2]([O:6][C:7](=[O:16])[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH:14]=O)[CH:9]=1)[CH2:3][CH2:4][CH3:5]>C(O)C.[Cl-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C1C=CC=CC=1>[CH2:2]([O:6][C:7](=[O:16])[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH:14]=[CH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:9]=1)[CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 2

HCID 5360545SodiumHCID 54078941HCID 54078941, compound

Product 1

HCID 54411654HCID 54411654, compoundYield 151.9%

Reagents, catalysts & solvents 2

HCID 70671Benzyltriphenylphosphonium chlorideCatalystHCID 702EthanolSolvent2×

Procedure

2.3 g (0.1 mol) of sodium were dissolved in 50 ml of ethanol and this solution was added dropwise to a solution of 38.9 g (0.1 mol) of benzyl-triphenyl-phosphonium chloride in 150 ml of ethanol at an internal temperature of -5° to 0° C. 20.6 g (0.1 mol) of 3-formyl-benzoic acid n-butyl ester were then added to this mixture and the mixture was kept at 0° to 5° C. for two hours, whilst stirring, and allowed to come slowly to room temperature. After concentrating the mixture, the residue was extracted with toluene, the toluene extract was filtered and the solvent was distilled off from the filtrate in vacuo. 21.3 g (75% theory) of 3-(2-phenyl-vinyl)-benzoic acid n-butyl ester were obtained as a slightly yellowish oil (cis/trans isomer mixture in the ratio 1:1).

Workup

  1. customto come slowly to room temperature
  2. concentrationAfter concentrating the mixture
  3. extractionthe residue was extracted with toluene
  4. extractionthe toluene extract
  5. filtrationwas filtered
  6. distillationthe solvent was distilled off from the filtrate in vacuo

Sources & evidence

ORD record
ord-51f5c21170ff43708b7bb654552ae073
Source dataset
uspto-grants-1981_06
Patent number
US04271186

Reaction notes

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