Hydrogen Peroxide → Guaiacylacetone

HRID 1680540Notes

Reaction equation

HRID 1680540 reaction equation
OO.[C:3]1([O:13][CH3:14])[C:4](=[CH:6][CH:7]=[C:8]([CH:12]=1)[CH:9]=[CH:10][CH3:11])[OH:5].S(=O)(=O)(O)[OH:16].C1(C)C=CC=CC=1>C(O)=O>[CH3:11][C:10]([CH2:9][C:8]1[CH:7]=[CH:6][C:4]([OH:5])=[C:3]([O:13][CH3:14])[CH:12]=1)=[O:16]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 1118Sulfuric AcidHCID 1140TolueneHCID 7338Isoeugenol

Product 1

HCID 17262GuaiacylacetoneYield 48%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent2×

Procedure

A solution of 30% aqueous hydrogen peroxide (9 ml, 85.5 mm) and formic acid (16 ml, 88%) is added to a solution of isoeugenol (8.1 gm, 50 mm) in formic acid (4 ml). The reaction mixture is stirred at 35° C.-40° C. under nitrogen atmosphere for 3 hours. The resulting 1-(4-hydroxy-3-methoxyphenyl)-propane-1,2-diol-monoformate is treated with 10% aqueous sulfuric acid (125 ml.) and toluene (125 ml.). After refluxing with mixing for 6 hours, the reaction mixture is cooled to room temperature, and the toluene layer separated. The aqueous layer is extracted with fresh toluene and the toluene layers are combined, washed with saturated aqueous sodium sulfate, dried over anhydrous sodium sulfate and concentrated to give methylvanillyl ketone in 48% yield.

Workup

  1. temperatureAfter refluxing
  2. additionwith mixing for 6 hours
  3. customthe toluene layer separated
  4. extractionThe aqueous layer is extracted with fresh toluene
  5. washwashed with saturated aqueous sodium sulfate
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-571fb4bb7d014ca28466792c4870b5d7
Source dataset
uspto-grants-1981_06
Patent number
US04273943

Reaction notes

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