Benzoic Acid → Benzoyl chloride

HRID 848690Notes

Reaction equation

HRID 848690 reaction equation
[C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N1C=CC(=O)C=C1)CCC.C(Cl)([Cl:23])=O>C1(C)C(C)=CC=CC=1>[C:1]([Cl:23])(=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 243Benzoic Acid2×HCID 6371Phosgene2×HCID 21854354HCID 21854354, compound

Product 1

HCID 7412Benzoyl chlorideYield 96%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

The procedure described in Example 1 was used and was applied to a solution of 1 mol of benzoic acid in 140 g of xylene. The reaction was carried out in the presence of 10 mmols of N-butyl-4-pyridone. 120 g of phosgene were introduced in the course of 2 hours 40 minutes. The yield obtained after distillation is 98.5%. Infra-red spectrometry did not reveal any trace of benzoic anhydride in the residue. The latter was recycled and a further batch of one mol of benzoic acid was introduced into the reactor. 120 g of phosgene are introduced in the course of 3 hours and the usual cycle is followed. A yield of 96% of benzoyl chloride was obtained after distillation. The residue still showed no traces of anhydride in infra-red spectrometry.

Workup

  1. customThe yield obtained
  2. distillationafter distillation

Sources & evidence

ORD record
ord-a73fc58458ef4359b5c314e2ff1fc9f7
Source dataset
uspto-grants-1981_10
Patent number
US04297301

Reaction notes

Loading…