Octanoic acid, 3,7-dimethyl- → Octanoic acid, 3,7-dimethyl-

HRID 1042374

Reaktionsgleichung

Reaktionsgleichung von HRID 1042374
[CH3:1][CH:2]([CH2:7][CH2:8][CH2:9][CH:10]([CH3:12])[CH3:11])[CH2:3][C:4]([OH:6])=[O:5]>S(Cl)(Cl)=O.O>[CH3:1][CH:2]([CH2:7][CH2:8][CH2:9][CH:10]([CH3:12])[CH3:11])[CH2:3][C:4]([OH:6])=[O:5].[C:4]([OH:6])(=[O:5])/[CH:3]=[C:2](/[CH2:7][CH2:8][CH:9]=[C:10]([CH3:11])[CH3:12])\[CH3:1]

Komponenten

5

Edukt 1

HCID 98008Octanoic acid, 3,7-dimethyl-

Produkt 2

HCID 98008Octanoic acid, 3,7-dimethyl-HCID 5275520Geranic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 24386Thionyl ChlorideLösungsmittel

Versuchsvorschrift

3,7-dimethyloctanoic acid was dissolved in thionyl chloride (10 ml) and treated in water bath for 3 hours to distill off excess thionyl chloride. Ethanol (30 ml) was added to chloride of 3,7-dimethyloctanoic acid and refluxed in water bath for 2 hours. After cooling, the reaction mixture was added to 1N HCl (80 ml) to be acidic and distributed with EtOAc. The distributed liquid was purified with column chromatography (developing solvent: C6H14-EtOAc (3:1)) after concentration, and the 3,7-dimethyloctanoic acid ethyl ester shown in the following was isolated. 3,7-dimethyloctanoic acid was obtained by contact reduction of geranic acid.

Aufarbeitung

  1. distillationto distill off excess thionyl chloride
  2. additionEthanol (30 ml) was added to chloride of 3,7-dimethyloctanoic acid
  3. temperaturerefluxed in water bath for 2 hours
  4. temperatureAfter cooling
  5. additionthe reaction mixture was added to 1N HCl (80 ml)
  6. customThe distributed liquid was purified with column chromatography (developing solvent: C6H14-EtOAc (3:1))
  7. concentrationafter concentration
  8. customfollowing was isolated

Quellen und Nachweise

ORD-Eintrag
ord-597a41b645544cb9bec224fdc815ca63
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08557864B2

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