Acetic Acid → 5,12-Dihydroxy-3,4-dihydrotetracene-2,6,11(1H)-trione

HRID 261158Notes

Reaction equation

HRID 261158 reaction equation
Cl[C:2]1[CH2:19][C:18]2[C:17]([OH:20])=[C:16]3[C:7]([C:8](=[O:22])[C:9]4[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=4[C:15]3=[O:21])=[C:6]([OH:23])[C:5]=2[CH2:4][CH:3]=1.C(O)(=[O:26])C>>[OH:23][C:6]1[C:5]2[CH2:4][CH2:3][C:2](=[O:26])[CH2:19][C:18]=2[C:17]([OH:20])=[C:16]2[C:7]=1[C:8](=[O:22])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=1[C:15]2=[O:21]

Participants

3

Reactant 2

HCID 176Acetic AcidHCID 20395213HCID 20395213, compound

Product 1

HCID 130132805,12-Dihydroxy-3,4-dihydrotetracene-2,6,11(1H)-trioneYield 76%

Procedure

There was prepared a mixture of glacial acetic acid (0.3 ml and concentrated sulfuric acid) 1.5 ml (which was cooled to 0° C. in an ice water bath). To this acid mixture was added 9-chloro-7,10-dihydro-6,11-dihydroxy-5,12-naphthacenedione (III) in a single batch and the mixture stirred. The mixture was permitted to warm slowly to ambient temperature over 3 hours at which temperature it was stirred for a further 24 hours. At the conclusion of this time the mixture was poured onto ice (ca. 25 g) and the organic layer extracted with chloroform (25 ml,×4) the chloroform extracts were combined, washed with saturated aqueous sodium bicarbonate, and with water, dried over anhydrous sodium sulfate, filtered, and the solvent removed from the filtrate under reduced pressure. The residue was washed with ether and further dried in vacuo to yield the "red ketone" 7,10-dihydro-6,11dihydroxy-5,9,12(8H)naphthacenetrione (IV) (18 mg, 76%). This product was shown to be homogeneous by thin layer chromatographic analysis and had the same Rf as an authentic sample (silica gel, 0.7% methanolic chloroform, Rf =0.59.

Workup

  1. customThere was prepared
  2. stirringwas stirred for a further 24 hours
  3. additionAt the conclusion of this time the mixture was poured onto ice (ca. 25 g)
  4. extractionthe organic layer extracted with chloroform (25 ml,×4) the chloroform extracts
  5. washwashed with saturated aqueous sodium bicarbonate
  6. dry with materialwith water, dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customthe solvent removed from the filtrate under reduced pressure
  9. washThe residue was washed with ether
  10. customfurther dried in vacuo

Sources & evidence

ORD record
ord-5a0551736359442db11d166ec21feb15
Source dataset
uspto-grants-1979_08
Patent number
US04164503

Reaction notes

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