Hydrogen Peroxide → Divanillin

HRID 1736265Notes

Reaction equation

HRID 1736265 reaction equation
[OH2:1].[O:2]=[CH:3][C:4]1[CH:12]=[CH:11][C:9]([OH:10])=[C:6]([O:7][CH3:8])[CH:5]=1.OO>C(O)(C)C>[CH3:8][O:7][C:6]1[CH:5]=[C:4]([CH:3]=[O:2])[CH:12]=[C:11]([C:11]2[C:9]([OH:1])=[C:6]([O:7][CH3:8])[CH:5]=[C:4]([CH:3]=[O:2])[CH:12]=2)[C:9]=1[OH:10]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 962WaterHCID 1183Vanillin

Product 1

HCID 95086DivanillinYield 82%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A 2 liter, round bottom flask was charged with 261.7 milligrams (13085 units) of medium purity, soybean peroxidase, 600 mL water, 900 mL isopropanol, and 157.36 grams (1.0342 moles) vanillin. The mixture was heated to 45°-50° C. Over 18-24 hours, 120 mL of 30% hydrogen peroxide was then metered into the reaction mixture. The product precipitated out of solution during peroxide addition affording 127.63 grams (82% theory) of dehydrodivanillin (CAS Registry No. 2092-49-1) which has the following chemical formula: ##STR10##

Workup

  1. temperatureThe mixture was heated to 45°-50° C
  2. customThe product precipitated out of solution during peroxide addition

Sources & evidence

ORD record
ord-77c0183787654f5d8f1da21e740fddad
Source dataset
uspto-grants-1996_07
Patent number
US05541033

Reaction notes

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