3-(3-Cyanophenyl)-2-propenoic acid → 3-Cyanobenzenepropanoic acid

HRID 231096Notes

Reaction equation

HRID 231096 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][CH:13]=1)[CH:6]=[CH:7][C:8]([OH:10])=[O:9])#[N:2]>O.[OH-].[Na+].[Pd]>[C:1]([C:3]1[CH:4]=[C:5]([CH2:6][CH2:7][C:8]([OH:10])=[O:9])[CH:11]=[CH:12][CH:13]=1)#[N:2]

Participants

5

Reactant 1

HCID 447258693-(3-Cyanophenyl)-2-propenoic acid

Product 1

HCID 138542693-Cyanobenzenepropanoic acid

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 3-cyano-cinnamic acid (11.5 g) in water (200 ml) and 2M sodium hydroxide solution (35 ml) was hydrogenated at 60 psi over 10% palladium on charcoal for 1.5 hours. The catalyst was filtered off and the filtrate was acidified with 2M hydrochloric acid to precipitate the product as a white solid, m.p. 103° C.

Workup

  1. filtrationThe catalyst was filtered off
  2. customto precipitate the product as a white solid, m.p. 103° C.

Sources & evidence

ORD record
ord-e0d85199d0754eb98fe2b02a4ba51a4d
Source dataset
uspto-grants-1989_07
Patent number
US04845110

Reaction notes

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