Hydrogen Peroxide → Isovanillic Acid

HRID 1803022Notes

Reaction equation

HRID 1803022 reaction equation
[O:1]=[CH:2][C:3]1[CH:11]=[CH:10][C:7]([O:8][CH3:9])=[C:5]([OH:6])[CH:4]=1.[OH-:12].[Na+].OO>CO>[OH:6][C:5]1[CH:4]=[C:3]([CH:11]=[CH:10][C:7]=1[O:8][CH3:9])[C:2]([OH:12])=[O:1]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 12127IsovanillinHCID 14798Sodium Hydroxide2×

Product 1

HCID 12575Isovanillic Acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methanol (350 ml), isovanillin (50 gm) and 30% methanolic sodium hydroxide solution (1 ml), were heated to 45° C. To this solution, 35% hydrogen peroxide solution (107 ml) was charged slowly maintaining pH at 10.5 to 11.5 using methanolic sodium hydroxide solution over a period of 2-3 hours. The reaction mass was quenched into chilled water (1 lt) and the pH adjusted to 2-3 using hydrochloric acid. The solids were filtered, washed with 50% aqueous methanol (50 ml) and dried at 45-50° C. to yield 3-hydroxy-4-methoxy benzoic acid.

Workup

  1. customThe reaction mass was quenched
  2. temperatureinto chilled water (1 lt)
  3. filtrationThe solids were filtered
  4. washwashed with 50% aqueous methanol (50 ml)
  5. customdried at 45-50° C.

Sources & evidence

ORD record
ord-a4ae5a1e824c4f2998c2e6bc097eb387
Source dataset
uspto-grants-2013_01
Patent number
US08350029B2

Reaction notes

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