Hydrochloric Acid → Benzophenone, 4-chloro-4'-methyl-
Reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[C:11]1([CH3:17])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[Al+3].[Cl-].[Cl-].[Cl-].Cl>O>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](=[O:7])[C:14]2[CH:15]=[CH:16][C:11]([CH3:17])=[CH:12][CH:13]=2)=[CH:4][CH:3]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
175 g of 4-chlorobenzoyl chloride are added dropwise at about 70° C. to a mixture of 553 g of toluene and 140 g of AlCl3. After completion of the evolution of HCl, the reaction mixture is added to 1 1 of water, and the solid obtained is separated off and recrystallized from 20 ethanol/toluene (50:1 parts by wt). 112.7 g of 4'-chloro-4-methylbenzophenone (melting point 129° C. to 130° C.; content of 4,4,-isomer>99.5% by GCSA) are obtained. 4-(4-Chlorobenzoyl)benzoic acid (melting point 256° C. to 258° C.) is accessible from this in 95% yield by oxidation. This acid is converted into the acid chloride by phosgenation. 97.7 g of 4-(4-chlorobenzoyl)benzoyl chloride, dissolved in 250.0 g of fluorobenzene, are added dropwise at 60° C. to 85° C. to a mixture of 254.5 g of fluorobenzene and 49.0 g of AlCl3. After the evolution of gas is complete, the reaction mixture is added to 0.5 1 of water and, after distillative removal of excess fluorobenzene, the precipitate is separated off, washed until neutral and recrystallized from chlorobenzene. Yield of 1-(4chlorobenzoyl-4-(4-fluorobenzoyl)benzene: 54.0 g (melting point 211° C. to 212° C.).
Workup
- customthe solid obtained
- customis separated off
- customrecrystallized from 20 ethanol/toluene (50:1 parts by wt)
Sources & evidence
- ORD record
- ord-d33036b99e0844eeb6f9d4b290649f05
- Source dataset
- uspto-grants-1994_04
- Patent number
- US05300693
Reaction notes
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