Hydrogen Peroxide → HCID 13231991, compound

HRID 1648946Notes

Reaction equation

HRID 1648946 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4](=[O:25])[CH:5]=[C:6]([C:13]1[C:21]([O:22][CH3:23])=[CH:20][C:19]([CH3:24])=[CH:18][C:14]=1[C:15]([OH:17])=[O:16])[C:7]2=[O:12].C(=O)([O-])[OH:27].[Na+].OO>CO>[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4](=[O:25])[CH:5]1[O:27][C:6]1([C:13]1[C:21]([O:22][CH3:23])=[CH:20][C:19]([CH3:24])=[CH:18][C:14]=1[C:15]([OH:17])=[O:16])[C:7]2=[O:12]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 156388WS-5995 BHCID 516892Sodium Bicarbonate

Product 1

HCID 13231991HCID 13231991, compoundYield 95.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In methanol (15 ml) was dissolved 2-(5-hydroxy-1,4-naphthoquinon-2-yl)-3-methoxy-5-methylbenzoic acid (100 mg) as obtained in Example 15, followed by addition of sodium hydrogen carbonate (80 mg). The mixture was stirred under ice-cooling. Then, 30% hydrogen peroxide (1.5 ml) was added dropwise and the reaction mixture was allowed to return gradually to room temperature, at which temperature it was further stirred for 5 hours. The solvent was then distilled off under reduced pressure, dilute HCl was added to the residue and the mixture was extracted with ethyl acetate. The extract was dried by addition of magnesium sulfate and the solvent was distilled off to give 2-(5-hydroxy-2,3-epoxy-1,4-dihydronaphthalene-1,4-dion-2-yl)-3-methoxy-5-methylbenzoic acid (100 mg). m.p. 267°-268° C.

Workup

  1. customas obtained in Example 15
  2. temperaturecooling
  3. customto return gradually to room temperature, at which temperature it
  4. stirringwas further stirred for 5 hours
  5. distillationThe solvent was then distilled off under reduced pressure, dilute HCl
  6. additionwas added to the residue
  7. extractionthe mixture was extracted with ethyl acetate
  8. dry with materialThe extract was dried by addition of magnesium sulfate
  9. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-1bcfbb0c340240f98faf9272dc1b259b
Source dataset
uspto-grants-1983_11
Patent number
US04414226

Reaction notes

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