Isopropyl iodide → 2-Cyano-3-methyl-2-(propan-2-yl)butanoic acid

HRID 262968Notes

Reaction equation

HRID 262968 reaction equation
[CH:1]([CH:4]([CH:7]([CH3:9])[CH3:8])[C:5]#[N:6])([CH3:3])[CH3:2].[Na].[CH:11](I)(C)C.[OH-:15].[Na+].[OH-:17].[K+]>>[CH:1]([C:4]([CH:7]([CH3:9])[CH3:8])([C:5]#[N:6])[C:11]([OH:17])=[O:15])([CH3:3])[CH3:2]

Participants

6

Reactant 5

HCID 6362Isopropyl iodideHCID 14797Potassium HydroxideHCID 14798Sodium HydroxideHCID 5360545SodiumHCID 136998413-Methyl-2-(propan-2-yl)butanenitrile

Product 1

HCID 3482772-Cyano-3-methyl-2-(propan-2-yl)butanoic acid

Procedure

Thus, MARSHALL prepares diisopropyl acetonitrile from a cyanacetic ester, by treating with sodium an alcoholic solution of this ester and by causing this mixture to react for several hours with an excess of isopropyl iodide. The monoalkylated product is eliminated by means of a 10% sodium hydroxide solution and the crude dialkyl ester obtained by this procedure is then treated with a 35% potassium hydroxide solution for 16 hours. After acidification, the diisopropyl cyanacetic acid obtained is decarboxylated by distillation in the presence of twice its weight of molten potassium hydroxide.

Workup

  1. customthe crude dialkyl ester obtained by this procedure

Sources & evidence

ORD record
ord-fd61993307604e76b794bb957af16dc1
Source dataset
uspto-grants-1979_05
Patent number
US04155929

Reaction notes

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