Water → HCID 583144, compound

HRID 1395599Notes

Reaction equation

HRID 1395599 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 tetrahydrofuran (THF) are added. The reaction is stirred overnight at RT and then poured into ether and water. The aqueous phase is washed (2×) 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 (2×) 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-89fb5b3ef637479d81f4d39d347a85d8
Source dataset
uspto-grants-1980_05
Patent number
US04204071

Reaction notes

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