p-Toluenesulfonic acid → HCID 18919716, compound

HRID 1490154Notes

Reaction equation

HRID 1490154 reaction equation
[CH3:1][O:2][C:3]1[CH:16]=[CH:15][C:6]([CH2:7][CH:8]2[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9]2)=[CH:5][CH:4]=1.[NH:17]1[CH2:21][CH2:20][CH2:19]C1.[C:22]1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[C:21]([CH:20]([CH3:22])[CH2:19][CH:10]1[CH2:9][CH:8]([CH2:7][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:16][CH:15]=2)[CH2:13][CH2:12][C:11]1=[O:14])#[N:17]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 31268PyrrolidineHCID 2817579HCID 2817579, compound

Product 1

HCID 18919716HCID 18919716, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-(4-Methoxybenzyl)cyclohexanone (10.25 g) was heated at reflux in toluene (500 ml) containing pyrrolidine (16 ml) and toluene-4-sulphonic acid (0.1 g). Water in the condensate was collected in a Dean and Stark apparatus. After 2 hours the solvent was removed by distillation until the reaction volume was approximately 100 ml. Ethanol (250 ml) and methacrylonitrile (20 ml) was added and the mixture heated at reflux for 16 hours, after which the solvent was evaporated under reduced pressure. The residue was dissolved in ethyl acetate and washed with 1M citric acid and saturated sodium carbonate solution. The organic phase was dried (MgSO4) and evaporated under reduced pressure to give 2-(2-cyanopropyl)-4-(4-methoxybenzyl)cyclohexanone (10.2 g).

Workup

  1. customWater in the condensate was collected in a Dean and Stark apparatus
  2. customAfter 2 hours the solvent was removed by distillation until the reaction volume
  3. additionEthanol (250 ml) and methacrylonitrile (20 ml) was added
  4. temperaturethe mixture heated
  5. temperatureat reflux for 16 hours
  6. customafter which the solvent was evaporated under reduced pressure
  7. dissolutionThe residue was dissolved in ethyl acetate
  8. washwashed with 1M citric acid and saturated sodium carbonate solution
  9. dry with materialThe organic phase was dried (MgSO4)
  10. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-354e79257e1e4d3e85654e39c27475ce
Source dataset
uspto-grants-1997_10
Patent number
US05681839

Reaction notes

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