Phosgene → 4-Benzoylbenzoyl chloride

HRID 6453

Reaction equation

HRID 6453 reaction equation
[C:1]([Cl:4])(Cl)=[O:2].O[C:6]1[CH:19]=[CH:18][C:9]([C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:11])=[CH:8][CH:7]=1>[Cl-].C([N+](C)(C)C)C1C=CC=CC=1.CC1C=CC=CC=1C>[Cl:4][C:1]([C:15]1[CH:16]=[CH:17][C:12]([C:10]([C:9]2[CH:18]=[CH:19][CH:6]=[CH:7][CH:8]=2)=[O:11])=[CH:13][CH:14]=1)=[O:2]

Participants

5

Reactant 2

HCID 6371Phosgene3×HCID 143474-Hydroxybenzophenone

Product 1

HCID 129121414-Benzoylbenzoyl chlorideYield 99.2%

Reagents, catalysts & solvents 2

HCID 5963Benzyltrimethylammonium chlorideCatalystHCID 7237O-XyleneSolvent

Procedure

A total of 3.4 kg of phosgene were passed in the course of 5 hours into a solution of 4 kg of 4-hydroxybenzophenone and 190 g of benzyltrimethylammonium chloride in 11.4 kg of o-xylene. During this time, the internal temperature was increased from 95° to 1200° C. After the end of the introduction of phosgene, stirring was continued for 30 minutes at 115° C. Working up was carried out by expelling the excess phosgene with nitrogen. The salt (catalyst) precipitated toward the end of the reaction was filtered off and the solvent was distilled off. 4.9 kg (93%) of yellowish 4-chloroformylbenzophenone of melting point 67°-72° C. were obtained. This crude product containing 12.69% of Cl- (theoretical value 13.60%) was used directly for the subsequent reactions, without further purification.

Workup

  1. temperatureDuring this time, the internal temperature was increased from 95° to 1200° C
  2. customThe salt (catalyst) precipitated toward the end of the reaction
  3. filtrationwas filtered off
  4. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-a09f60cece474e8a9b8d9edbc056d2df
Source dataset
uspto-grants-1993_09
Patent number
US05248805

Linked notes

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