4-Chlorobiphenyl → 2-[2-(4'-Chloro-biphenyl-4-YL)-2-oxo-ethyl]acrylic acid

HRID 1386845

Reaktionsgleichung

Reaktionsgleichung von HRID 1386845
[Cl-].[Al+3].[Cl-].[Cl-].[C:5]1(=[O:12])[O:11][C:9](=[O:10])[CH2:8][C:6]1=[CH2:7].[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:16][CH:15]=1>ClC1C=CC=CC=1>[Cl:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]2[CH:25]=[CH:24][C:23]([C:9](=[O:10])[CH2:8][C:6](=[CH2:7])[C:5]([OH:11])=[O:12])=[CH:22][CH:21]=2)=[CH:18][CH:19]=1

Komponenten

5

Edukt 3

HCID 163234-ChlorobiphenylHCID 75110Itaconic AnhydrideHCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 98393182-[2-(4'-Chloro-biphenyl-4-YL)-2-oxo-ethyl]acrylic acidAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7964ChlorobenzeneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

21.2 g of anhydrous aluminum chloride are introduced into 130 g of chlorobenzene and the mixture is cooled to 0° C. A solid mixture of 8.3 g of itaconic anhydride and 13.2 g of 4-chlorobiphenyl is added in portions in the course of one hour. The reaction mixture is stirred at 0° C. for three hours and then added to ice water. The solid reaction product is filtered off and washed twice with water (50 ml). The product is dried at room temperature and about 100 mbar until free of solvent and water. 4-(4′-Chlorobiphenyl-4-yl)-4-keto-2-methylenebutyric acid is obtained in a yield of 75% as a colorless, finely crystalline powder.

Aufarbeitung

  1. additionis added in portions in the course of one hour
  2. customThe solid reaction product
  3. filtrationis filtered off
  4. washwashed twice with water (50 ml)
  5. customThe product is dried at room temperature

Quellen und Nachweise

ORD-Eintrag
ord-aea2525ceec34293be55e14484e9db21
Quelldatensatz
uspto-grants-2001_07
Patentnummer
US06265607B1

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