HCID 76667863, compound → HCID 58029314, compound

HRID 1877719Notes

Reaction equation

HRID 1877719 reaction equation
[CH3:1][C:2]([CH2:6][CH2:7][C:8]([CH3:12])=[C:9]([CH3:11])[CH3:10])=[CH:3][C:4]#[N:5].[H][H]>[Pd].C(OCC)(=O)C>[CH3:1][CH:2]([CH2:6][CH2:7][CH:8]([CH3:12])[CH:9]([CH3:11])[CH3:10])[CH2:3][C:4]#[N:5]

Participants

5

Reactant 2

HCID 76667863HCID 76667863, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 58029314HCID 58029314, compoundYield 98.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

3,6,7-Trimethyl-2,6-octadienenitrile (15 g; 0.092 mol), palladium on charcoal (5% Pd/C, 1.5 g) and ethyl acetate (60 ml) were charged in a 500 ml stirred autoclave and hydrogenated (4 bar hydrogen) at 25° C. for 24 hours. Filtration over celite and removal of the solvent afforded 15.1 g of the saturated nitrile as a mixture of two isomers. Distillation using a 10 cm Vigreux column gave 13.8 g of 98.2% pure 3,6,7-trimethyloctanenitrile (mixture of isomers; 56/42) in a yield of 88%.

Workup

  1. filtrationFiltration
  2. customover celite and removal of the solvent

Sources & evidence

ORD record
ord-1a9ecb7327f84b2f91c4350e86535b01
Source dataset
uspto-grants-2012_11
Patent number
US08313736B2

Reaction notes

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