Water → 2-Benzyl-2-methyl-3-butenitrile

HRID 1732144

Reaction equation

HRID 1732144 reaction equation
O.[CH2:2](Cl)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:10][C:11](=[CH:14][CH3:15])[C:12]#[N:13].[OH-].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH3:10][C:11]([CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)([CH:14]=[CH2:15])[C:12]#[N:13]

Participants

7

Reactant 4

HCID 962WaterHCID 7503Benzyl ChlorideHCID 14798Sodium HydroxideHCID 299352-Methyl-2-butenenitrile

Product 1

HCID 54638042-Benzyl-2-methyl-3-butenitrile

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent

Procedure

Into a 500 ml 4-neck flask, equipped with a stirrer, reflux cooler, dropping funnel and water separator, 126.5 g (1 mole) of benzylchloride, 81 g (1 mole) of 2-methyl-2-butene-nitrile, 100 ml of toluene, and 10 g of tetrabutylammonium bromide were first introduced and heated to reflux. To this mixture, 40 g (1 mole) of solid sodium hyroxide were added in portions. The reaction mixture was then maintained one more hour at reflux. Thereupon, it was washed to neutrality with water, the phases were separated and the organic phase distilled as described in Example 1. The yield in desired product was 103.5 g, corresponding to 61% of the theoretical.

Workup

  1. customInto a 500 ml 4-neck flask, equipped with a stirrer
  2. temperaturereflux cooler
  3. temperatureheated to reflux
  4. temperatureThe reaction mixture was then maintained one more hour
  5. temperatureat reflux
  6. washThereupon, it was washed
  7. customthe phases were separated
  8. distillationthe organic phase distilled

Sources & evidence

ORD record
ord-e90031ab58bd475f9e2ba9098024d0ba
Source dataset
uspto-grants-1986_11
Patent number
US04625046

Linked notes

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