Quinone → HCID 86586142, compound

HRID 1837408Notes

Reaction equation

HRID 1837408 reaction equation
C([C:5]1[CH:18]=[CH:17][C:16]2[C:7](=[CH:8][C:9]3[C:14]([CH:15]=2)=[CH:13][C:12](C(C)(C)C)=CC=3)[CH:6]=1)(C)(C)C.[C:23]1(=[O:30])[CH:28]=[CH:27][C:26](=[O:29])[CH:25]=[CH:24]1>>[C:23]1(=[O:30])[C:28]2[C:9]3[CH:8]=[C:7]4[C:16]([CH:17]=[CH:18][CH:5]=[CH:6]4)=[CH:15][C:14]=3[CH:13]=[CH:12][C:27]=2[C:26](=[O:29])[CH:25]=[CH:24]1

Participants

3

Reactant 2

HCID 4650QuinoneHCID 157404162,6-Di-tert-butylanthracene

Product 1

HCID 86586142HCID 86586142, compound

Procedure

6,14-di-tert-butyl-9,10-dihydro-9,10[1′,2′]benzenoanthracene-1,4-diol 45 is illustrated in FIG. 9F. 2,6-di-tert-butyl-anthracene (19.0 g, 0.0654 mol) and 1,4-benzoquinone (7.78 g, 0.072 mol) in xylenes (150 ml) was heated to reflux for 2 h. Solvent was removed in vacuo and the crude product was purified by flash chromatography (2:3, hexane:dichloromethane) to give benzenoanthracene-1,4-dione, which was dissolved in acetic acid (150 ml) and heated to reflux and a drop of aqueous HBr (48%). After 10 min, the reaction was cooled and water was added. Precipitates were collected and dried to give compound 45 as an off-white solid (12.73 g, 0.0319 mol, 49%).

Workup

  1. temperatureto reflux for 2 h
  2. customSolvent was removed in vacuo
  3. customthe crude product was purified by flash chromatography (2:3, hexane:dichloromethane)

Sources & evidence

ORD record
ord-a622d3a21a7a45588c1f7692a965bb91
Source dataset
uspto-grants-2004_08
Patent number
US06783814B2

Reaction notes

Loading…