1-Bromopropane → 2-Cyano-2-propylpentanoic acid

HRID 262969Notes

Reaction equation

HRID 262969 reaction equation
[CH3:1]CCBr.[I-].[CH2:6]([CH:9]([CH2:12][CH2:13][CH3:14])[C:10]#[N:11])[CH2:7][CH3:8].[OH-:15].[Na+].[OH-:17].[K+].[Na]>>[CH2:6]([C:9]([CH2:12][CH2:13][CH3:14])([C:10]#[N:11])[C:1]([OH:17])=[O:15])[CH2:7][CH3:8]

Participants

7

Reactant 6

HCID 78401-BromopropaneHCID 14797Potassium Hydroxide2×HCID 14798Sodium HydroxideHCID 30165Iodide IonHCID 833302-PropylvaleronitrileHCID 5360545Sodium

Product 1

HCID 218964722-Cyano-2-propylpentanoic acid

Procedure

Process for the preparation of di-n-propylacetonitrile of the formula: ##STR5## whereby, (a) sodium n-propylate in n-propanol medium is added to a reaction medium which is formed of a cyanacetate of general formula: ##STR6## in which R represents an alkyl radical having from 1 to 4 carbon atoms, and n-propyl bromide or iodide, the alkylation reaction taking place under reflux at atmospheric pressure, (b) the crude ester obtained is saponified at a temperature between 30° and 70° C. with a 10 to 20% by weight solution of sodium hydroxide or potassium hydroxide in the proportion of 1.25 to 2 mols of sodium or potassium hydroxide per mol of crude ester, the resulting salt is acidified with a strong acid at a temperature not exceeding 40° C., to give crude di-n-propyl cyanacetic acid, (c) which is decarboxylated solely by heating, in the absence of any supplementary agent, at a temperature between 140° C. and 190° C., so as to obtain the di-n-propylacetonitrile.

Workup

  1. customthe alkylation reaction
  2. customobtained
  3. customexceeding 40° C.

Sources & evidence

ORD record
ord-3d5e917bfe414c35a738b4f13080d7b6
Source dataset
uspto-grants-1979_05
Patent number
US04155929

Reaction notes

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