Hydrogen Peroxide → 2,3-Epoxy-2-methyl-1,4-naphthoquinone

HRID 879020

Reaction equation

HRID 879020 reaction equation
[CH3:1][C:2]1[C:12](=[O:13])[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:4](=[O:5])[CH:3]=1.[OH-:14].[Na+].OO>CO.O>[CH3:1][C:2]12[C:12](=[O:13])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:4](=[O:5])[CH:3]1[O:14]2

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 4055MenadioneHCID 14798Sodium Hydroxide

Product 1

HCID 858452,3-Epoxy-2-methyl-1,4-naphthoquinoneYield 91.5%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

Menadione crystalline (1) (5 g, 29.04 mmol, 1 equivalent) and 2 M NaOH (7.26 mL, 14.52 mmol, 0.5 equivalents) are dissolved in a mixture of methanol/water 4:1 (50 mL) at 0-2° C. After stirring at this temperature for 10 minutes, 35% hydrogen peroxide is added (4.2 mL, 43.56 mmol, 1.5 equivalents). Work-up: after 30 minutes at 0° C. the product is extracted with ethyl ether. The organic phase is dried over Na2SO4 and evaporated under reduced pressure. A whitish powder is obtained (5 g, 26.57 mmol). Yield: 91.5%.

Workup

  1. extractionafter 30 minutes at 0° C. the product is extracted with ethyl ether
  2. dry with materialThe organic phase is dried over Na2SO4
  3. customevaporated under reduced pressure
  4. customA whitish powder is obtained (5 g, 26.57 mmol)

Sources & evidence

ORD record
ord-a7e61bb52da04aeb97d2f2e8f4e6d445
Source dataset
uspto-grants-2015_03
Patent number
US08987503B2

Linked notes

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