Toluene → N-[2-(1-cyclohexen-1-yl)-1-cyclohexen-1-yl]hexanamide

HRID 435810

Reaction equation

HRID 435810 reaction equation
[C:1]1([CH:7]2[CH2:12][CH2:11][CH2:10][CH2:9][C:8]2=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.[C:14]([NH2:21])(=[O:20])[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].C1(C)C=CC=CC=1>O>[C:1]1([C:7]2[CH2:12][CH2:11][CH2:10][CH2:9][C:8]=2[NH:21][C:14](=[O:20])[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 12332HexanamideHCID 101175Cyclohexenylcyclohexanone

Product 1

HCID 21481520N-[2-(1-cyclohexen-1-yl)-1-cyclohexen-1-yl]hexanamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-(1-Cyclohexenyl)cyclohexanone (17.8 g., 0.1 mole), hexanamide (11.5 g., 0.1 mole), 5.0 g. of a highly acidic resin, Amberlyst 15, and toluene (150 ml) are mixed, stirred and heated at reflux for 16 hours. The water formed in the course of the reaction is azeotroped from the reaction mixture. The hot solution is decanted from the Amberlyst catalyst, the catalyst washed with toluene (200 ml.), and the toluene fractions are combined. Pentane (300 ml.) is added to the toluene solution, the mixture chilled in ice and filtered to remove 3.65 g. of unreacted hexanamide. The orange filtrate is stripped to yield 24 g. of crude product, an oil.

Workup

  1. temperatureheated
  2. temperatureat reflux for 16 hours
  3. customis azeotroped from the reaction mixture
  4. customThe hot solution is decanted from the Amberlyst catalyst
  5. washthe catalyst washed with toluene (200 ml.)
  6. additionPentane (300 ml.) is added to the toluene solution
  7. temperaturethe mixture chilled in ice
  8. filtrationfiltered
  9. customto remove 3.65 g
  10. customto yield 24 g

Sources & evidence

ORD record
ord-f96a01e1938a476f950aff32e9e0c337
Source dataset
uspto-grants-1977_02
Patent number
US04006236

Linked notes

Loading…