Water → 2-(4-Carboxyphenoxy)-4-chlorobenzoic acid

HRID 1605169Notes

Reaction equation

HRID 1605169 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:10]=2[C:11]([OH:13])=[O:12])=[CH:4][CH:3]=1.[Mn]([O-])(=O)(=O)=[O:20].[K+].C(O)(C)(C)C.[OH2:30]>>[C:1]([C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:10]=2[C:11]([OH:13])=[O:12])=[CH:4][CH:3]=1)([OH:20])=[O:30]

Participants

5

Reactant 4

HCID 962WaterHCID 6386tert-ButanolHCID 516875Potassium PermanganateHCID 12650295HCID 12650295, compound

Product 1

HCID 215496502-(4-Carboxyphenoxy)-4-chlorobenzoic acid

Procedure

A mixture of 12 g. of 2-(p-methylphenyloxy)-4-chlorobenzoic acid, 72 g. of potassium permanganate, 200 ml. of t-butanol and 350 ml. of water is refluxed for 4.5 hours. After this time, the t-butanol is distilled off, and the reaction mixture is filtered. The filtrate is acidified to give 2-(p-carboxyphenyloxy)-4-chlorobenzoic acid which can be recrystallized from benzene:heptane.

Workup

  1. additionA mixture of 12 g
  2. distillationAfter this time, the t-butanol is distilled off
  3. filtrationthe reaction mixture is filtered

Sources & evidence

ORD record
ord-9602467da31f45d48e410d2b254d23cd
Source dataset
uspto-grants-1976_04
Patent number
US03949084

Reaction notes

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