HCID 67401990, compound → HCID 68496213, compound

HRID 1514029Notes

Reaction equation

HRID 1514029 reaction equation
[CH3:1][C@@H:2]1[CH:7]=[CH:6][CH2:5][C:4]([CH3:9])([CH3:8])[C@H:3]1[CH2:10][C:11]#[N:12]>CCOC(C)=O.[Pd]>[CH3:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][C:4]([CH3:8])([CH3:9])[C@H:3]1[CH2:10][C:11]#[N:12]

Participants

4

Reactant 1

HCID 67401990HCID 67401990, compound

Product 1

HCID 68496213HCID 68496213, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of trans-(2,6,6-trimethyl-3-cyclohexen-1-yl)acetonitrile obtained in Example 3b) (3.0 g, purity 98%, 18 mmol) in AcOEt (30 ml) was added 10% Pd—C and the mixture was shaken under H2 (1 atm) at room temperature during 3 days. The catalyst was filtered off through celite and the filtrate was concentrated. Bulb-to-bulb distillation (oven temp 80° C./0.3 mbar) afforded trans-(2,6,6,trimethylcyclohexyl)acetonitrile (2.88 g, purity 99%, yield 98%).

Workup

  1. filtrationThe catalyst was filtered off through celite
  2. concentrationthe filtrate was concentrated
  3. distillationBulb-to-bulb distillation (oven temp 80° C./0.3 mbar)

Sources & evidence

ORD record
ord-05a2a76670ba41718a74b720b67ceee8
Source dataset
uspto-grants-2012_07
Patent number
US08222198B2

Reaction notes

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