Hydrochloric Acid → 4-Acetyl-4-pentylheptanedinitrile

HRID 1285033Notes

Reaction equation

HRID 1285033 reaction equation
[CH3:1][C:2](=[O:9])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[OH-].[K+].CO.[C:14](#[N:17])[CH:15]=[CH2:16].Cl>C(O)(C)(C)C>[C:2]([C:3]([CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])([CH2:16][CH2:15][C:14]#[N:17])[CH2:16][CH2:15][C:14]#[N:17])(=[O:9])[CH3:1]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7855AcrylonitrileHCID 80932-OctanoneHCID 23689386Potassium hydroxide methanol

Product 1

HCID 126597364-Acetyl-4-pentylheptanedinitrile

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent2×

Conditions

Temperature
5 °C

Procedure

In a flask, 600 g of 2-octanone (CH3 (CH2)5COCH3), 500 g of tert-butanol ((CH3)3COH) and 30 g of a KOH/CH3OH solution were mixed and then stirred under ice-cooling. To the resulting solution was added dropwise a solution of 375 g of acrylonitrile (CH2 =CHCN) in 400 g of (CH3)3COH while maintaining the temperature at 5° C. or lower. After completion of the addition, the resulting solution was further stirred continuously for 1 hour, after which this reaction solution was made neutral by addition of dilute hydrochloric acid. The deposited salt was separated by filtration, and the residue was distilled under reduced pressure to obtain 3-acetyl-1,5-dicyano-3-pentylpentane.

Workup

  1. temperaturecooling
  2. additionAfter completion of the addition
  3. stirringthe resulting solution was further stirred continuously for 1 hour
  4. customThe deposited salt was separated by filtration
  5. distillationthe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-5076c0ff9d294d62af09070583187dd7
Source dataset
uspto-grants-1986_01
Patent number
US04564694

Reaction notes

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