Thionyl Chloride → 2,4-Pentadienoyl chloride, 5-phenyl-

HRID 462031

Reaktionsgleichung

Reaktionsgleichung von HRID 462031
[CH:1](=[CH:10][C:11]([OH:13])=O)[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.S(Cl)([Cl:16])=O>C1C=CC=CC=1>[CH:1](=[CH:10][C:11]([Cl:16])=[O:13])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Komponenten

4

Edukt 2

HCID 24386Thionyl ChlorideHCID 737775-Phenyl-2,4-pentadienoic acid

Produkt 1

HCID 30848092,4-Pentadienoyl chloride, 5-phenyl-Ausbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

8.7 g of cinnamylideneacetic acid was added to 100 ml of benzene and then an excessive amount of thionyl chloride (1.2 molar equivalent to cinnamylideneacetic acid) was added dropwise to the mixture while heating to 70°-90° C and stirring the mixture to form a cinnamylideneacetic acid chloride. By distilling off the solvent from the reaction product, yellow crystals having a melting point of about 60° C were obtained. The crystals were dissolved in 20 ml of methyl ethyl ketone and then 8 g of hydroxyethyl methacrylate was added slowly to the solution with stirring under ice-cooling. After further stirring under ice-cooling for about 20 minutes, 50 ml of pyridine was added slowly to the mixture as a hydrogen chloride accepting agent to conduct esterification. When the reaction product was treated with diluted (5%) hydrochloride acid, crystals were formed, which were recovered and recrystallized from hexane to provide crystals of a monomer having a melting point of 51°-52.5° C with a yield of 94%.

Aufarbeitung

  1. temperaturewhile heating to 70°-90° C

Quellen und Nachweise

ORD-Eintrag
ord-8a666bd5f87446788026c0b1fbd12db5
Quelldatensatz
uspto-grants-1977_12
Patentnummer
US04065430

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