Potassium Permanganate → 3-Benzoyloxy-4-methoxybenzoic acid

HRID 1584926Notes

Reaction equation

HRID 1584926 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-87fec72fbdf64521b36a9c9f790e2ecb
Source dataset
uspto-grants-1999_08
Patent number
US05935978

Reaction notes

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