HCID 14180568, compound → 2H-1,3-Benzodioxole-4,7-dione

HRID 1904959Notes

Reaction equation

HRID 1904959 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[C:11]2[O:16][CH2:17][O:18][C:10]=12)C1C=CC=CC=1>O1CCCC1.[Pd]>[CH2:17]1[O:16][C:11]2[C:12](=[O:15])[CH:13]=[CH:14][C:9](=[O:8])[C:10]=2[O:18]1

Participants

4

Reactant 1

HCID 14180568HCID 14180568, compound

Product 1

HCID 128387792H-1,3-Benzodioxole-4,7-dioneYield 102.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-benzyloxy-2,3-methylenedioxyphenol (7.7 g) in tetrahydrofuran (50 ml) was hydrogenated at atmospheric pressure over palladium-on-carbon overnight. The catalyst was removed by filtration, and the resulting hydroquinone intermediate was oxidized in actonitrile solution with ceric ammonium nitrate (25 g). After 5 minutes the reaction was quenched with water and extracted with ethyl acetate. Evaporation of the organic extract and chromatography afforded 4.9 g of 2,3-methylenedioxy-1,4-benzoquinone, mp 106°-7° C.

Workup

  1. customThe catalyst was removed by filtration
  2. customAfter 5 minutes the reaction was quenched with water
  3. extractionextracted with ethyl acetate
  4. customEvaporation of the
  5. extractionorganic extract

Sources & evidence

ORD record
ord-becab1f0c62a478b88ab4f9f29948c80
Source dataset
uspto-grants-1989_06
Patent number
US04840965

Reaction notes

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