Sodium Hydroxide → Isobutylmalonic acid

HRID 444191

Reaction equation

HRID 444191 reaction equation
C([O:3][C:4]([CH:6]([CH2:12][CH:13]([CH3:15])[CH3:14])[C:7]([O:9]CC)=[O:8])=[O:5])C.[OH-].[Na+]>CO>[C:7]([CH:6]([CH2:12][CH:13]([CH3:15])[CH3:14])[C:4]([OH:5])=[O:3])([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 25047Diethyl isobutylmalonate

Product 1

HCID 78069Isobutylmalonic acidYield 100.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 91.1 g of 2-(ethyloxycarbonyl)-4-methylpentanoic acid, ethyl ester in 300 ml of methanol is treated for 6 hours at 80° C. with 400 ml of 10% sodium hydroxide. The solution is concentrated in vacuo to 400 ml and acidified with 10% hydrochloric acid. The product is extracted with ethyl acetate to yield 67.6 g of the title compound, which crystallizes on standing. Recrystallization from ethyl acetate-hexane yields the title compound, melting point 102°-105° C.

Workup

  1. concentrationThe solution is concentrated in vacuo to 400 ml
  2. extractionThe product is extracted with ethyl acetate

Sources & evidence

ORD record
ord-aba4e87484d749a19d784f4fd13ccc12
Source dataset
uspto-grants-1981_04
Patent number
US04263293

Linked notes

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