Reacción #1178404

Ecuación de reacción

4-Benzoylbenzoic acid

thionyl chloride

toluene

→

4-Benzoylbenzoyl Chloride

Rendimiento 91.0%

Disolventes

Dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroequipped
2. 2
   Temperaturawith reflux condenser and overhead stirrer
3. 3
   Temperaturathe mixture was heated
4. 4
   Temperaturaat reflux for 4 hours
5. 5
   TemperaturaAfter cooling
6. 6
   Otrothe solvents were removed under reduced pressure
7. 7
   Otrothe residual thionyl chloride was removed by three evaporations
8. 8
   OtroThe product was recrystallized from 1:4 toluene
9. 9
   Otrohexane to give 988 g (91% yield)
10. 10
    Otroafter drying in a vacuum oven
11. 11
    OtroThe final compound was stored for use in the preparation of a monomer

Procedimiento

4-Benzoylbenzoic acid (BBA), 1.0 kg (4.42 moles), was added to a dry 5 liter Morton flask equipped with reflux condenser and overhead stirrer, followed by the addition of 645 ml (8.84 moles) of thionyl chloride and 725 ml of toluene. Dimethylformamide, 3.5 ml, was then added and the mixture was heated at reflux for 4 hours. After cooling, the solvents were removed under reduced pressure and the residual thionyl chloride was removed by three evaporations using 3×500 ml of toluene. The product was recrystallized from 1:4 toluene:hexane to give 988 g (91% yield) after drying in a vacuum oven. Product melting point was 92-94° C. Nuclear magnetic resonance (NMR) analysis (1H NMR (CDCl3)) was consistent with the desired product: aromatic protons 7.20-8.25 (m, 9H). All chemical shift values are in ppm downfield from a tetramethylsilane internal standard. The final compound was stored for use in the preparation of a monomer used in the synthesis of Compound III.

Fuente