Hydrochloric Acid → Phenyl-3-chlorobenzoate

HRID 400259Notes

Reaction equation

HRID 400259 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](Cl)=[O:6].[C:11]1([OH:17])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.N1C=CC=CC=1.Cl>C1(C)C=CC=CC=1>[C:11]1([O:17][C:5](=[O:6])[C:4]2[CH:8]=[CH:9][CH:10]=[C:2]([Cl:1])[CH:3]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 996PhenolHCID 1049PyridineHCID 69252Benzoyl chloride, 3-chloro-

Product 1

HCID 11984386Phenyl-3-chlorobenzoate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Phenyl-3-chlorobenzoate is prepared by reacting 3-chlorobenzoyl chloride with phenol in toluene with some pyridine (1 mol equivalent per acid chloride) to trap the HCl that evolves. After aqueous extraction of the pyridinium salt and any excess starting materials, the product is crystallized from the toluene solution.

Workup

  1. extractionAfter aqueous extraction of the pyridinium salt
  2. customany excess starting materials, the product is crystallized from the toluene solution

Sources & evidence

ORD record
ord-5580efed7c9e466188dccb287d2def56
Source dataset
uspto-grants-1998_10
Patent number
US05827927

Reaction notes

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