1-(But-3-en-1-yl)-1,4-dihydroanthracene-9,10-dione → 1-Butyl-1,2,3,4-tetrahydroanthracene-9,10-dione

HRID 1657890Notes

Reaction equation

HRID 1657890 reaction equation
[CH2:1]([CH:5]1[C:18]2[C:17](=[O:19])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](=[O:20])[C:9]=2[CH2:8][CH:7]=[CH:6]1)[CH2:2][CH:3]=[CH2:4].[H][H]>[Pd].C(OCC)(=O)C>[CH2:1]([CH:5]1[C:18]2[C:17](=[O:19])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](=[O:20])[C:9]=2[CH2:8][CH2:7][CH2:6]1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 214906241-(But-3-en-1-yl)-1,4-dihydroanthracene-9,10-dioneHCID 178418361HCID 178418361, compound

Product 1

HCID 214906221-Butyl-1,2,3,4-tetrahydroanthracene-9,10-dioneYield 83%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A 5.0 g. sample of 1,4-dihydro-1-(3-butenyl)anthraquinone (6a, R = H) was dissolved in 100 ml. of ethyl acetate. The solution was then hydrogenated using 0.2 g. 10% Pd/C catalyst. After the absorption of three equivalents of hydrogen, the mixture was filtered to remove the catalyst. It was then stirred at room temperature overnight while exposed to air to oxidize the hydroquinone. After removal of the solvent, the residue was recrystallized from methanol to give 4.2 g. product (83% yield). The gas chromatographic retention time, infrared spectrum, and nmr spectrum of this sample were identical with those of an authentic sample.

Workup

  1. filtrationthe mixture was filtered
  2. customto remove the catalyst
  3. customAfter removal of the solvent
  4. customthe residue was recrystallized from methanol
  5. customto give 4.2 g

Sources & evidence

ORD record
ord-4706733e8d2f46a39a26791ec09db01c
Source dataset
uspto-grants-1976_06
Patent number
US03962288

Reaction notes

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