Hydroquinone → 4-Cyclohexyl-4-oxobutanenitrile

HRID 1417043Notes

Reaction equation

HRID 1417043 reaction equation
[C:1]1(=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:8](#[N:11])[CH:9]=[CH2:10].C1(N)CCCCC1.[C:19]1(C=CC(O)=CC=1)[OH:20]>C(O)(=O)C>[CH2:2]1[CH2:3][CH2:4][CH2:5][CH2:6][CH:1]1[C:19]([CH2:10][CH2:9][C:8]#[N:11])=[O:20]

Participants

6

Reactant 4

HCID 785HydroquinoneHCID 7855AcrylonitrileHCID 7965CyclohexylamineHCID 7967Cyclohexanone

Product 1

HCID 117689094-Cyclohexyl-4-oxobutanenitrile

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
130 °C

Procedure

A reactor is loaded with 980 g of cyclohexanone, 22 g of acrylonitrile, 18 g of glacial acetic acid, 40 g of cyclohexylamine and 11 g of hydroquinone. The reaction mixture is slowly raised to 130° C. and then kept at this temperature for 2 hours. The reaction product is cooled to 25° C., the catalyst is filtered out and distillation is performed, collecting 552 g of 3-(2-cyclohexanoly)propionitrile (b.p. 113-116° C./4 mm Hg).

Workup

  1. temperatureThe reaction product is cooled to 25° C.
  2. filtrationthe catalyst is filtered out
  3. distillationdistillation
  4. customcollecting 552 g of 3-(2-cyclohexanoly)propionitrile (b.p. 113-116° C./4 mm Hg)

Sources & evidence

ORD record
ord-ed4e0704a1214b14bb38b7f135d1d074
Source dataset
uspto-grants-1999_06
Patent number
US05917067

Reaction notes

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