Phosgene → 4-Benzoylbenzoyl chloride

HRID 486860

Reaction equation

HRID 486860 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 was passed through a solution of 4 kg of 4-hydroxybenzophenone and 190 g of benzyltrimethylammonium chloride in 11.4 kg of o-xylene over a period of 5 hours, during which time the internal temperature was raised from 95° to 120° C. The introduction of phosgene was then stopped, and stirring was continued for 30 minutes at 115° C. Before the product was worked up, the excess phosgene was expelled with nitrogen. The salt (catalyst) which precipitated toward the end of the reaction was filtered off, and the solvent was removed by distillation. There were obtained 4.9 kg (93%) of yellowish 4-chloroformylbenzophenone having a melting point of 67°-72° C. This crude product having a Cl content of 12.69% (theory=13.60%) was used unpurified as starting material for subsequent reactions.

Workup

  1. temperaturethe internal temperature was raised from 95° to 120° C
  2. customThe salt (catalyst) which precipitated toward the end of the reaction
  3. filtrationwas filtered off
  4. customthe solvent was removed by distillation

Sources & evidence

ORD record
ord-3b637853f62e4aacababa0234e5bd8df
Source dataset
uspto-grants-1994_03
Patent number
US05292915

Linked notes

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