Hydrochloric Acid → Phenyl-3-chlorobenzoate

HRID 1379171Notes

Reaction equation

HRID 1379171 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-a72bec2b35324f4898b73d1b1039779c
Source dataset
uspto-grants-1997_09
Patent number
US05670564

Reaction notes

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