2,2-dimethylhexanedinitrile → HCID 11815890, compound

HRID 1699123Notes

Reaction equation

HRID 1699123 reaction equation
CC(C)([O-:4])C.[K+].[CH3:7][C:8]([CH3:16])([CH2:11][CH2:12][CH2:13][C:14]#[N:15])[C:9]#N>C1(C)C=CC=CC=1>[C:14]([CH:13]1[C:7](=[O:4])[C:8]([CH3:16])([CH3:9])[CH2:11][CH2:12]1)#[N:15]

Participants

4

Reactant 2

HCID 2642192,2-dimethylhexanedinitrileHCID 23665647Potassium tert-butoxide

Product 1

HCID 11815890HCID 11815890, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A suspension of potassium t-butoxide (60.2 g, 0.54 mole) in toluene is treated with 2,2-dimethyladiponitrile (120.7 g, 0.87 mole) at 80° C., stirred for 2 hours, cooled to less than 30° C., and quenched with water. The phases are separated, the organic phase is stirred with 3N hydrochloric acid and filtered. The filtrate is concentrated in vacuo to give an oil which is distilled (2 torr, 150° C.) twice to afford the title product as a colorless oil, 65.7 g (98.5% pure, 55% yield), identified by gas chromatography.

Workup

  1. temperaturecooled to less than 30° C.
  2. customquenched with water
  3. customThe phases are separated
  4. stirringthe organic phase is stirred with 3N hydrochloric acid
  5. filtrationfiltered
  6. concentrationThe filtrate is concentrated in vacuo
  7. customto give an oil which
  8. distillationis distilled (2 torr, 150° C.) twice

Sources & evidence

ORD record
ord-4ef161acf469414ba17ef971bbc10a74
Source dataset
uspto-grants-2002_02
Patent number
US06344580B1

Reaction notes

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