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

HRID 1386844

Reaktionsgleichung

Reaktionsgleichung von HRID 1386844
[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.S(=O)(=O)(O)O>ClC1C=CC=CC=1Cl.O>[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

7

Edukt 4

HCID 1118Sulfuric AcidHCID 163234-ChlorobiphenylHCID 75110Itaconic AnhydrideHCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 98393182-[2-(4'-Chloro-biphenyl-4-YL)-2-oxo-ethyl]acrylic acidAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 72391,2-DichlorobenzeneLösungsmittel2×

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

193.3 g (1.45 mol) of anhydrous aluminum chloride are introduced in 1100 g of o-dichlorobenzene and the mixture is brought to 45° C. with stirring. A solution of 80.9 g (0.72 mol) of itaconic anhydride and 132 g (0.7 mol) of 4-chlorobiphenyl in 700 g of o-dichlorobenzene at 50° C. is added dropwise in the course of three hours. The reaction mixture is stirred at 25° C. for four hours and then added to an ice-cold mixture of 1000 g of water and 25 g of sulfuric acid (96%). The aqueous phase is separated off. The organic phase is washed three times with a mixture of 1000 g of water and 15 g of sulfuric acid (96%) in each case. After washing three times, it is allowed to cool to approximately 20° C. and the colorless product is then filtered off with suction. This is then washed three times with 150 g of ethanol (96%) in each case. The product is dried at 60° C. and about 100 mbar until free of solvent and water. 148 g (0.49 mol) of 4-(4′-chlorobiphenyl-4-yl)-4-keto-2-methylenebutyric acid (70%) are obtained as a colorless, finely crystalline powder. By working up the mother liquor, as described in Example 1, the yield is increased to 83%. (HPLC purity 99.6-99.8%)

Aufarbeitung

  1. customis brought to 45° C.
  2. stirringThe reaction mixture is stirred at 25° C. for four hours
  3. customThe aqueous phase is separated off
  4. washThe organic phase is washed three times
  5. additionwith a mixture of 1000 g of water and 15 g of sulfuric acid (96%) in each case
  6. washAfter washing three times, it
  7. filtrationthe colorless product is then filtered off with suction
  8. washThis is then washed three times with 150 g of ethanol (96%) in each case
  9. customThe product is dried at 60° C.

Quellen und Nachweise

ORD-Eintrag
ord-a74e8711005a41babc26262c51ad049b
Quelldatensatz
uspto-grants-2001_07
Patentnummer
US06265607B1

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