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

HRID 1386847Notes

Reaction equation

HRID 1386847 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].ClC1C=CC(C)=CC=1.[C:13]1(=[O:20])[O:19][C:17](=[O:18])[CH2:16][C:14]1=[CH2:15].[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[CH:24][CH:23]=1>>[Cl:21][C:22]1[CH:23]=[CH:24][C:25]([C:28]2[CH:33]=[CH:32][C:31]([C:17](=[O:18])[CH2:16][C:14](=[CH2:15])[C:13]([OH:19])=[O:20])=[CH:30][CH:29]=2)=[CH:26][CH:27]=1

Participants

5

Reactant 4

HCID 78104-ChlorotolueneHCID 163234-ChlorobiphenylHCID 75110Itaconic AnhydrideHCID 6451240Aluminum(III) Chloride

Product 1

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

Conditions

Temperature
40 °C

Procedure

21.2 g of anhydrous aluminum chloride are introduced into 50 g of p-chlorotoluene and the mixture is heated to 40° C. with stirring. 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 40° C. for 30 minutes and then added to 100 g of 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 70% as a colorless, finely crystalline powder.

Workup

  1. additionis added in portions in the course of one hour
  2. stirringThe reaction mixture is stirred at 40° C. for 30 minutes
  3. customThe solid reaction product
  4. filtrationis filtered off
  5. washwashed twice with water (50 ml)
  6. customThe product is dried at room temperature

Sources & evidence

ORD record
ord-7dc1a2d638ed46a9b88ca2914096d488
Source dataset
uspto-grants-2001_07
Patent number
US06265607B1

Reaction notes

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