1,4-Anthraquinone → 2-Benzylthionaphthacene-5,12-dione

HRID 1084469

Reaction equation

HRID 1084469 reaction equation
[CH2:1]([S:8][C:9]1[CH:14]=[CH:13]O[C:11](=O)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:16]1(=[O:31])[C:29]2[C:20](=[CH:21][C:22]3[C:27]([CH:28]=2)=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:19](=[O:30])[CH:18]=C1>C1C(Cl)=CC=C(Cl)C=1.O=[Mn]=O>[CH2:1]([S:8][C:9]1[CH:14]=[CH:13][C:18]2[C:19](=[O:30])[C:20]3[C:29](=[CH:28][C:27]4[C:22]([CH:21]=3)=[CH:23][CH:24]=[CH:25][CH:26]=4)[C:16](=[O:31])[C:11]=2[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 694571,4-AnthraquinoneHCID 146427864-Benzylthio-2-oxo-2H-pyran

Product 1

HCID 200635452-Benzylthionaphthacene-5,12-dione

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 46851,4-DichlorobenzeneSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 0.27 g (0.0012 mol) of 4-benzylthio-2-oxo-2H-pyrane, 0.25 g (0.0012 mol) of 1,4-anthraquinone and 0.10 g (0.0012 mol) of MnO2 in 5 ml of dichlorobenzene is heated for 24 hours under reflux (180° C.), then cooled and chromatographed over silica gel. Using cyclohexane as eluant, dichlorbenzene is first extracted, then the crude product is chromatographed with CH2Cl2. The pre-purified product is chromatographed once more, using CH2Cl2 as eluant, and the solvent is removed by evaporation. Yield: 0.09 g (20%). Melting point: 200°-203° C.

Workup

  1. temperatureis heated for 24 hours
  2. temperaturecooled
  3. customchromatographed over silica gel
  4. extractionUsing cyclohexane as eluant, dichlorbenzene is first extracted
  5. customthe crude product is chromatographed with CH2Cl2
  6. customThe pre-purified product is chromatographed once more
  7. customthe solvent is removed by evaporation

Sources & evidence

ORD record
ord-31ac7a23f62340e896052fd1f43801c3
Source dataset
uspto-grants-1991_04
Patent number
US05004814

Linked notes

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