Thionyl Chloride → HCID 20745768, Verbindung

HRID 2307935Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2307935
[CH3:1][C:2]([C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1)([CH3:7])[CH2:3][C:4](O)=[O:5].S(Cl)([Cl:17])=O>CN(C=O)C.C1C=CC=CC=1>[CH3:1][C:2]([C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1)([CH3:7])[CH2:3][C:4]([Cl:17])=[O:5]

Komponenten

5

Edukt 2

HCID 24386Thionyl Chloride2×HCID 38711363-methyl-3-(4-methylphenyl)butanoic acid

Produkt 1

HCID 20745768HCID 20745768, VerbindungAusbeute 107,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideKatalysatorHCID 241BenzeneLösungsmittel

Versuchsvorschrift

A solution containing 3-methyl-3-(4-methylphenyl)butyric acid (8.5 g, 44.2 mmol) and anhydrous DMF (5 drops) in anhydrous benzene (110 mL) was refluxed under nitrogen as thionyl chloride (8.1 mL, 110 mmol)was added dropwise under nitrogen. The solution was refluxed an additional 15 h after complete addition of thionyl chloride. The dark brownish reaction mixture was allowed to cool to room temperature and concentrated under vacuum. TLC analysis of the crude material showed complete disappearance of the starting material. Presence of DMF was evident from the proton NMR. The crude material, 3-methyl-3-(4-methylphenyl)butyric acid chloride (305) (about 10 g), thus obtained was used in the next step without further purification.

Aufarbeitung

  1. additionwas added dropwise under nitrogen
  2. temperatureThe solution was refluxed an additional 15 h
  3. customThe dark brownish reaction mixture
  4. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-24534b4b69a340cfa50104867f4a54e4
Quelldatensatz
uspto-grants-2004_12
Patentnummer
US06833372B2

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