Thionyl Chloride → 3-Benzoylacrylyl chloride

HRID 1703319Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1703319
[C:1]([CH:9]=[CH:10][C:11]([OH:13])=O)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:16])=O>C(Cl)Cl>[C:1]([CH:9]=[CH:10][C:11]([Cl:16])=[O:13])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 24386Thionyl ChlorideHCID 94714Beta-benzoylacrylic acid

Produkt 1

HCID 573021923-Benzoylacrylyl chloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

3-Benzoylacrylic acid (3 g.) was refluxed for 2 hours with 100 ml. of methylene chloride and 10 ml. thionyl chloride. Concentration to dryness gave 3-benzoylacrylyl chloride. Methanol (15 ml.) was added and the resulting solution stirred for 0.5 hour. Ether (35 ml.) was added. The resulting organic mixture was washed in sequence with 15 ml. of water, 15 ml. of 1 N sodium hydroxide and twice with 15 ml. of water, concentrated to an oil, the oil triturated with 25 ml. of hot hexane, decanted from insolubles and the hexane concentrated to yield methyl 3-benzoylacrylate (1.9 g., oil, m/e 190).

Aufarbeitung

  1. concentrationConcentration to dryness

Quellen und Nachweise

ORD-Eintrag
ord-d4c4c4aa8e3840318a5ec0d29972669a
Quelldatensatz
uspto-grants-1982_09
Patentnummer
US04351843

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