Phenylacetonitrile → HCID 13642035, compound

HRID 1979498Notes

Reaction equation

HRID 1979498 reaction equation
[OH-].[Na+].[CH2:3]([C:10]#[N:11])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>[Br-].C([N+](C)(C)C)CCCCCCCCCCCCCCC>[CH3:5][C:4]([CH3:9])=[CH:3][CH2:10][CH:3]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[C:10]#[N:11]

Participants

4

Reactant 2

HCID 8794PhenylacetonitrileHCID 14798Sodium Hydroxide

Product 1

HCID 13642035HCID 13642035, compoundYield 119.8%

Reagents, catalysts & solvents 1

HCID 5974Hexadecyltrimethylammonium BromideCatalyst

Procedure

384 g (4.8 mol) of 50% sodium hydroxide and 12 g of hexadecyl-trimethylammonium bromide are placed in a 2-liter flask provided with a thermometer, stirrer and reflux condenser and there is added dropwise while stirring within 0.25 hour a mixture of 469 g of benzyl cyanide (4 mol) and 502 g (4.8 mol) of prenyl chloride(1). During the addition the mixture warms and it is subsequently stirred for a further 3 hours at 60° C. After cooling, the mixture is poured on to 500 g of ice, extracted four times with ether and washed neutral with water. The phase separation can be facilitated by the addition of a small amount of alcohol. After drying over sodium sulphate, the ether is evaporated and the residue is fractionally distilled. There are obtained 444 g of 5-methyl-2-phenyl-4-hexene nitrile of boiling point 108°-109° C./3 mmHg; nD20 =1.5171-72; yield 60%.

Workup

  1. customprovided with a thermometer, stirrer
  2. temperaturereflux condenser
  3. additionthere is added dropwise
  4. additionDuring the addition the mixture warms and it
  5. stirringis subsequently stirred for a further 3 hours at 60° C
  6. temperatureAfter cooling
  7. extractionextracted four times with ether
  8. washwashed neutral with water
  9. customThe phase separation
  10. additioncan be facilitated by the addition of a small amount of alcohol
  11. dry with materialAfter drying over sodium sulphate
  12. customthe ether is evaporated
  13. distillationthe residue is fractionally distilled

Sources & evidence

ORD record
ord-9fc8ca81c5334bab958cf01d1792c7b5
Source dataset
uspto-grants-1984_11
Patent number
US04481133

Reaction notes

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