8-Cyanooct-7-enoic acid → 8-Cyano-octanoic acid

HRID 1417045Notes

Reaction equation

HRID 1417045 reaction equation
[C:1]([CH:3]=[CH:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([OH:12])=[O:11])#[N:2]>C1(C)C=CC=CC=1.[Pd]>[C:1]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([OH:12])=[O:11])#[N:2]

Participants

4

Reactant 1

HCID 541765898-Cyanooct-7-enoic acid

Product 1

HCID 110843008-Cyano-octanoic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1140TolueneSolvent

Procedure

167 g of 8-cyano-7-octenoic acid dissolved in 800 ml of toluene are hydrogenated selectively at 2 bar in an autoclave in the presence of 10 g of Pd on charcoal at 5% at 50° C. for 5 hours. After filtration of the catalyst and evaporation of the solvent, 165 g of an oil that distills at 150° C. at 0.05 torr are recovered. The product has been identified as 8-cyanooctanoic acid by I.R. (film) analysis techniques: 3400, 3000, 2950, 2875, 2260, 1710, 1430 cm-1 and mass spectrometry by electron-impact ionization (70 eV): 170, 152, 140, 123, 110, 94, 83, 69, 55, 41. Analytically calculated values for C9H15NO2 (169.22): C 63.88%, H 8.93%, N 8.28%. Found: C 63.76%, H 9.12%, N 8.37%.

Workup

  1. filtrationAfter filtration of the catalyst and evaporation of the solvent, 165 g of an oil
  2. distillationthat distills at 150° C. at 0.05 torr
  3. customare recovered

Sources & evidence

ORD record
ord-f6a6e17b9f2d451c883876a79023bbeb
Source dataset
uspto-grants-1999_06
Patent number
US05917067

Reaction notes

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