Potassium Permanganate → 3-Benzoyloxy-4-methoxybenzoic acid

HRID 1870364Notes

Reaction equation

HRID 1870364 reaction equation
[Mn]([O-])(=O)(=O)=[O:2].[K+].[C:7]([O:15][C:16]1[CH:21]=[C:20]([CH:22]=[O:23])[CH:19]=[CH:18][C:17]=1[O:24][CH3:25])(=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>CC(C)=O>[C:7]([O:15][C:16]1[CH:21]=[C:20]([CH:19]=[CH:18][C:17]=1[O:24][CH3:25])[C:22]([OH:2])=[O:23])(=[O:14])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 516875Potassium PermanganateHCID 9581385-Formyl-2-methoxyphenyl benzoate

Product 1

HCID 211879403-Benzoyloxy-4-methoxybenzoic acid

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A stirred solution of potassium permanganate (28 g) in acetone (200 mL) is treated with 2-methoxy-5-formylphenyl benzoate (35.2 g; that is prepared as described in Reference Example 8), and the resulting vigorously reacting mixture is cooled in an ice bath. It is then stirred at room temperature for 3 hours. The mixture is then concentrated and the residue is treated with saturated aqueous sodium metabisulfite solution (300 mL). The resulting white solid is filtered off, washed well with water (200 mL), and dried, to give 3-benzoyloxy-4-methoxy-benzoic acid (29.3 g), m.p. 180-183° C.

Workup

  1. customthat is prepared
  2. temperatureis cooled in an ice bath
  3. concentrationThe mixture is then concentrated
  4. additionthe residue is treated with saturated aqueous sodium metabisulfite solution (300 mL)
  5. filtrationThe resulting white solid is filtered off
  6. washwashed well with water (200 mL)
  7. customdried

Sources & evidence

ORD record
ord-52fa016e2a3042aab6fe0e70a21838a2
Source dataset
uspto-grants-2000_08
Patent number
US06096768

Reaction notes

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