Water → HCID 583144, compound

HRID 2286788Notes

Reaction equation

HRID 2286788 reaction equation
[OH:1][C:2]([CH:4]=[CH2:5])=[O:3].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:25]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)(=O)[CH3:26].CCOCC.O>CS(C)=O.O1CCCC1>[C:28]1([C:25]([CH3:26])=[CH:5][CH2:4][C:2]([OH:1])=[O:3])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

7

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 7410AcetophenoneHCID 23462488HCID 23462488, compound

Product 1

HCID 583144HCID 583144, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (1.70 g., 57% in oil dispersion) is washed free of oil using hexane under nitrogen, and then 7.4 g (20 mmole) of triphenylphosphine hydroxycarbonylethylene and 2.4 g (20 mmole) of acetophenone in 25 ml of dimethylsulfoxide (DMSO) and 20 ml of tetrahydrofuran (THF) are added. The reaction is stirred overnight at RT and then poured into ether and water. The aqueous phase is washed (2X) with ether and then acidified with 2 N sulfuric acid followed by extraction into ether. The organic phase is washed with water, dried over calcium sulfate and solvent removed to give 4-phenyl-3-pentenoic acid.

Workup

  1. washSodium hydride (1.70 g., 57% in oil dispersion) is washed free of oil
  2. washThe aqueous phase is washed (2X) with ether
  3. extractionfollowed by extraction into ether
  4. washThe organic phase is washed with water
  5. dry with materialdried over calcium sulfate and solvent
  6. customremoved

Sources & evidence

ORD record
ord-d614743477df40258370d3ac9a00bec2
Source dataset
uspto-grants-1981_05
Patent number
US04267359

Reaction notes

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