Toluene → 4,7,9,9-Tetramethyldec-3-enenitrile

HRID 1461575Notes

Reaction equation

HRID 1461575 reaction equation
[CH3:1][CH:2]([CH2:5][CH2:6][CH:7]([CH3:13])[CH2:8][C:9]([CH3:12])([CH3:11])[CH3:10])[CH:3]=O.[C:14]([CH2:16]C(O)=O)#[N:15].C1(C)C=CC=CC=1.C([O-])(=O)C.[NH4+]>CN(C)C=O>[CH3:1][C:2]([CH2:5][CH2:6][CH:7]([CH3:13])[CH2:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[CH:3][CH2:16][C:14]#[N:15]

Participants

6

Reactant 4

HCID 1140TolueneHCID 9740Cyanoacetic acidHCID 517165Ammonium AcetateHCID 199810432,5,7,7-Tetramethyloctanal

Product 1

HCID 538051294,7,9,9-Tetramethyldec-3-enenitrileYield 91.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
180 °C

Procedure

438 g (2.38 moles) of 2,5,7,7-tetramethyloctanal, 202 g (2.38 moles) of cyanoacetic acid, 350 ml of toluene, 350 ml of dimethylformamide and 28.5 g of ammonium acetate were heated under a water separator for 4 h, while stirring. Thereafter, the toluene was distilled off and the remaining residue was heated for 2 h at 180° C. The cooled residue was poured onto ice water and 10 extracted with diethyl ether. The organic phase was washed in succession with NaHCO: solution and water and then distilled. 450 g (yield: 91% of theory) of 4,7,9,9-tetramethyldec-3-enenitrile of boiling point 83°-88° C./-.3 mbar were obtained. The fragrance note was waxy, floral and fresh.

Workup

  1. distillationThereafter, the toluene was distilled off
  2. additionThe cooled residue was poured onto ice water and 10
  3. extractionextracted with diethyl ether
  4. washThe organic phase was washed in succession with NaHCO
  5. distillationsolution and water and then distilled

Sources & evidence

ORD record
ord-b04c9731b4074a9fbf1f665ed9302cec
Source dataset
uspto-grants-1991_12
Patent number
US05075489

Reaction notes

Loading…