Toluene → 4-Benzoylbenzoyl chloride

HRID 1586208Notes

Reaction equation

HRID 1586208 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 photoactivatable chain transfer reagents, as described for instance in Examples 4 and 6.

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 photoactivatable chain transfer reagents

Sources & evidence

ORD record
ord-945ed45e140b40a993760b2494ec2d45
Source dataset
uspto-grants-1999_08
Patent number
US05942555

Reaction notes

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