Anthrarufin → 1,5-Dihydroxyanthrone

HRID 1440438

Reaction equation

HRID 1440438 reaction equation
[OH:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[C:9]([OH:17])[CH:10]=[CH:11][CH:12]=3)[C:7](=O)[C:6]=2[CH:5]=[CH:4][CH:3]=1>C(O)(=O)C.Cl>[OH:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[C:9]([OH:17])[CH:10]=[CH:11][CH:12]=3)[CH2:7][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 8328Anthrarufin

Product 1

HCID 134867781,5-DihydroxyanthroneYield 85%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent

Conditions

Temperature
5 °C

Procedure

To a suspension of 1,5-dihydroxyanthraquinone (10 g, 41.6 mmole) and stannous chloride (45 g, 237 mmole) in glacial acetic acid (150 ml), conc. hydrochloric acid (90 ml) was added at 16°-20° C. The resulting mixture was stirred for 4 hours under reflux. After standing at room temperature overnight, the reaction mixture was cooled to 5° C. A precipitate was filtered, washed with H2O and dried to afford 8.0 g of 1,5-dihydroxyanthrone as dark brown needles having a m.p. of 231°-233° C.

Workup

  1. additionwas added at 16°-20° C
  2. temperatureunder reflux
  3. waitAfter standing at room temperature overnight
  4. filtrationA precipitate was filtered
  5. washwashed with H2O
  6. customdried

Sources & evidence

ORD record
ord-0161266de26e4b34a9813d39dd795e33
Source dataset
uspto-grants-1996_03
Patent number
US05498748

Linked notes

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