Toluene → 4-Benzoylbenzoyl chloride

HRID 991399Notes

Reaction equation

HRID 991399 reaction equation
[C:1]([C:9]1[CH:17]=[CH:16][C:12]([C:13](O)=[O:14])=[CH:11][CH:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:20])=O.C1(C)C=CC=CC=1>CN(C)C=O>[C:1]([C:9]1[CH:17]=[CH:16][C:12]([C:13]([Cl:20])=[O:14])=[CH:11][CH:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 691474-Benzoylbenzoic acid

Product 1

HCID 129121414-Benzoylbenzoyl chlorideYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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 at 80 MHz (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 photoactivatable polymers as described, for instance, in Example 3.

Workup

  1. customequipped
  2. temperaturewith reflux condenser and overhead stirrer
  3. temperaturethe mixture was heated
  4. temperatureat reflux for 4 hours
  5. temperatureAfter cooling
  6. customthe solvents were removed under reduced pressure
  7. customthe residual thionyl chloride was removed by three evaporations
  8. customThe product was recrystallized from 1:4 toluene
  9. customhexane to give 988 g (91 % yield)
  10. customafter drying in a vacuum oven
  11. customThe final compound was stored for use in the preparation of a monomer
  12. customused in the synthesis of photoactivatable polymers

Sources & evidence

ORD record
ord-cf5c885e0f8c435295e4e871d7a84dfe
Source dataset
uspto-grants-2002_10
Patent number
US06465178B2

Reaction notes

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