Benzoic Acid → Benzoyl chloride

HRID 1657935Notes

Reaction equation

HRID 1657935 reaction equation
[C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)([Cl:12])=O.CP(=O)(C)CCl>ClC1C=CC=CC=1>[C:1]([Cl:12])(=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 243Benzoic Acid2×HCID 6371PhosgeneHCID 74224Phosphine oxide, (chloromethyl)dimethyl-

Product 1

HCID 7412Benzoyl chloride

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

In the device described for example 1, 122 g of benzoic acid are reacted with phosgene after having added 0.1 g of dimethyl-chloromethyl-phosphine oxide. At the beginning the operation is carried out at a temperature just above the melting point of the benzoic acid (122°C), but while the reaction is continuing the temperature is brought down to approx. 100°C. So as to avoid sublimation, it is useful to add to the reation mixture approx. 20 g of chlorobenzene. The phosgene absorption is terminated after abt. 2 hours. After a postreaction of another hour a more then 99% crude yield of a slightly colored benzoyl chloride is obtained which, for further purification, may be submitted to further distillation under reduced pressure. The net yield is abt. 136 g corresponding to 97% theoretical yield.

Workup

  1. customis brought down to approx. 100°C
  2. customThe phosgene absorption
  3. customis terminated after abt
  4. custom2 hours

Sources & evidence

ORD record
ord-1934f10c85f94a45a16b03644d573d7d
Source dataset
uspto-grants-1976_06
Patent number
US03962326

Reaction notes

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