Methyl iodide → 2,2-Dimethylhexanenitrile

HRID 1389174

Reaction equation

HRID 1389174 reaction equation
[CH3:1][C:2]([CH3:9])([CH2:5][CH2:6][CH2:7][CH3:8])[CH2:3][NH2:4].C(#N)CCCCC.CI.[NH2-].[Na+]>O.C1(C)C=CC=CC=1>[CH3:1][C:2]([CH3:9])([CH2:5][CH2:6][CH2:7][CH3:8])[C:3]#[N:4]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 12352HexanenitrileHCID 24533Sodium amideHCID 543253312,2-Dimethylhexan-1-amine

Product 1

HCID 35735622,2-DimethylhexanenitrileYield 81%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Procedure

2,2-Dimethylhex-1-ylamine. A solution of capronitrile (25 g., 0.26 mole) and methyl iodide (75 g., 0.53 mole) in 80 ml. of dry toluene is warmed to 80° and treated gradually with a suspension of sodium amide (25.4 g., 0.65 mole) in 100 ml. of toluene at a rate sufficient to maintain general reflux. After addition is complete, the mixture is stirred and refluxed for an additional 2 hr. period, cooled and treated with 150 ml. of water. The organic layer is separated, washed with water and dried over magnesium sulfate. Concentration of the dried solution under reduced pressure and distillation of residual material affords an 81% yield of 2,2-dimethylcapronitrile.

Workup

  1. temperaturereflux
  2. additionAfter addition
  3. temperaturerefluxed for an additional 2 hr
  4. temperatureperiod, cooled
  5. additiontreated with 150 ml
  6. customThe organic layer is separated
  7. washwashed with water
  8. dry with materialdried over magnesium sulfate
  9. distillationConcentration of the dried solution under reduced pressure and distillation of residual material

Sources & evidence

ORD record
ord-b10eaa5a65e849c58391f3ae0f7ee78e
Source dataset
uspto-grants-1981_01
Patent number
US04243681

Linked notes

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