Diethyl isopentylmalonate → (3-Methylbutyl)propanedioic acid

HRID 373864

Reaction equation

HRID 373864 reaction equation
[CH2:1]([CH:6]([C:12]([O:14]CC)=[O:13])[C:7]([O:9]CC)=[O:8])[CH2:2][CH:3]([CH3:5])[CH3:4]>[OH-].[Na+]>[CH2:1]([CH:6]([C:12]([OH:14])=[O:13])[C:7]([OH:9])=[O:8])[CH2:2][CH:3]([CH3:5])[CH3:4]

Participants

3

Reactant 1

HCID 79384Diethyl isopentylmalonate

Product 1

HCID 278478(3-Methylbutyl)propanedioic acid

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

Diethyl isoamylmalonate (71.7 g) was added to a 50% aqueous solution of sodium hydroxide (60 ml), and the mixture was heated under reflux for 6 h. After cooling, the mixture was extracted with ether; the water layer was acidified with hydrochloric acid and, after saturation with sodium chloride, was extracted with ether. The extracts from the acidic aqueous layer were concentrated under reduced pressure to give isoamylmalonic acid. The obtained dicaboxylic acid was heated at 180° C. for 2 h. After distillation under reduced pressure, 5-mehyl-caproic acid was obtained. Yield: 30 g (75%), b.p. 107°-108° C./11 mmHg.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 6 h
  3. temperatureAfter cooling
  4. extractionthe mixture was extracted with ether
  5. extractionafter saturation with sodium chloride, was extracted with ether
  6. concentrationThe extracts from the acidic aqueous layer were concentrated under reduced pressure

Sources & evidence

ORD record
ord-32c405820f6c4f5c82850fd63b706a04
Source dataset
uspto-grants-1992_11
Patent number
US05166174

Linked notes

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