Diethyl isopentylmalonate → (3-Methylbutyl)propanedioic acid

HRID 22418

Reaktionsgleichung

Reaktionsgleichung von HRID 22418
[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]

Komponenten

3

Edukt 1

HCID 79384Diethyl isopentylmalonate

Produkt 1

HCID 278478(3-Methylbutyl)propanedioic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-f93cd37270844637b1dc71386708c419
Quelldatensatz
uspto-grants-1995_06
Patentnummer
US05428062

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