4-tert-Butylcyclohexanone → 3,3',3'',3'''-(5-tert-Butyl-2-oxocyclohexane-1,1,3,3-tetrayl)tetrapropanenitrile

HRID 867045Notes

Reaction equation

HRID 867045 reaction equation
[C:1]([CH:5]1[CH2:10][CH2:9][C:8](=[O:11])[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[OH-].[K+].[C:14](#[N:17])[CH:15]=[CH2:16]>C(O)(C)(C)C>[C:1]([CH:5]1[CH2:6][C:7]([CH2:16][CH2:15][C:14]#[N:17])([CH2:16][CH2:15][C:14]#[N:17])[C:8](=[O:11])[C:9]([CH2:16][CH2:15][C:14]#[N:17])([CH2:16][CH2:15][C:14]#[N:17])[CH2:10]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 73924-tert-ButylcyclohexanoneHCID 7855AcrylonitrileHCID 14797Potassium Hydroxide

Product 1

HCID 203171723,3',3'',3'''-(5-tert-Butyl-2-oxocyclohexane-1,1,3,3-tetrayl)tetrapropanenitrileYield 75.2%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A solution of 4-t-butylcyclohexanone (15.4g) and crushed KOH (0.5g) in tert.butanol (62.4g) was stirred and kept at or below 30° C. while acrylonitrile (21.2g) was added dropwise. During the addition a solid began to precipitate. When addition was complete the thick slurry was stirred for a further hour before the solid was collected by filtration. The solid was washed with water, then crystallised from 2-ethoxyethanol to yield 27.5g of 4-t-butyl-2,2,6,6-tetra(β-cyanoethyl)cyclohexanone, m.p. 175°-178° C.

Workup

  1. custombelow 30° C.
  2. additionwas added dropwise
  3. additionDuring the addition a solid
  4. customto precipitate
  5. additionWhen addition
  6. stirringwas stirred for a further hour before the solid
  7. filtrationwas collected by filtration
  8. washThe solid was washed with water
  9. customcrystallised from 2-ethoxyethanol

Sources & evidence

ORD record
ord-7007bf7277be499192aed1f994b6736b
Source dataset
uspto-grants-1978_07
Patent number
US04102701

Reaction notes

Loading…