Hydrochloric Acid → 3-(1-formylcyclohexyl)propanenitrile

HRID 2164725Notes

Reaction equation

HRID 2164725 reaction equation
[CH:1]1([CH:7]=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[K+].[C:11](#[N:14])[CH:12]=[CH2:13].Cl>CCOCC>[C:11]([CH2:12][CH2:13][C:1]1([CH:7]=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)#[N:14]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7855AcrylonitrileHCID 14797Potassium HydroxideHCID 16275Cyclohexanecarboxaldehyde

Product 1

HCID 111828113-(1-formylcyclohexyl)propanenitrileYield 38%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of cyclohexane-carboxaldehyde (100 g.; 0.89 mole) and 50% potassium hydroxide solution (10.2 g.) is added, dropwise, acrylonitrile (50.4 g.; 0.95 mole) over the course of one hour, maintaining the reaction temperature between 50°-60° C. by occasional cooling. After all has been added, the mixture is stirred for an additional one hour until the exotherm ceases and then heated to 50°-60° C. for 30 minutes. The product is acidified with dilute hydrochloric acid, taken up into ether, washed with water, dried (MgSO4) and distilled to afford 38% of colorless 1-(2-cyanoethyl)-1-formylcyclohexane (55.4 g.), b.p. 142°-146° C./5 mm.

Workup

  1. additionAfter all has been added
  2. temperatureheated to 50°-60° C. for 30 minutes
  3. washwashed with water
  4. dry with materialdried (MgSO4)
  5. distillationdistilled

Sources & evidence

ORD record
ord-f2d33e2695ce446d956d4403783bf314
Source dataset
uspto-grants-1985_03
Patent number
US04507291

Reaction notes

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