2-Oxo-4-phenylbut-3-enoic acid → 2-Oxo-4-phenylbutyric acid

HRID 1032046Notes

Reaction equation

HRID 1032046 reaction equation
[CH:1](=[CH:8][C:9](=[O:13])[C:10]([OH:12])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>C(O)C.[PdH2]>[C:2]1([CH2:1][CH2:8][C:9](=[O:13])[C:10]([OH:12])=[O:11])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 2434352-Oxo-4-phenylbut-3-enoic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 697322-Oxo-4-phenylbutyric acid

Reagents, catalysts & solvents 2

HCID 13628823Pd(II)-hydrideCatalystHCID 702EthanolSolvent

Procedure

Benzalpyruvic acid (2-oxo-4-phenyl-3-butenoic acid) prepared as in step B of Example 2 (26.4 g, 0.15 mol) was dissolved in 150 ml ethanol. The catalyst from Example 1 was then added to the unsaturated acid. The reactor was pressurized to 10 psi with hydrogen and aged with good agitation for two hours. The catalyst was then removed by filtration and the titled product isolated in quantitative yield following vacuum concentration. 1H NMR (CDCl3, DMSO-d6) δ: 3.9 (m, 4H), 7.3 (s, 5H), 10.9 (s, 1H). IR (KBr) cm-1 : 3500m, 3000m, 1725s, 1700s, 1600m, 1200s, 970m.

Workup

  1. customThe catalyst was then removed by filtration

Sources & evidence

ORD record
ord-794386f68ade42f79a953f04d8e1d942
Source dataset
uspto-grants-1990_09
Patent number
US04956490

Reaction notes

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