Sodium → HCID 21514903, compound

HRID 1576258Notes

Reaction equation

HRID 1576258 reaction equation
[CH3:1][O:2][C:3]1[C:16]2[C:15](=O)[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8]([CH2:22][C:23]([OH:25])=[O:24])([CH2:18][C:19]([OH:21])=[O:20])[C:7]=2[CH:6]=[CH:5][CH:4]=1.[Na]>C(O)CCC>[CH3:1][O:2][C:3]1[C:16]2[CH2:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8]([CH2:22][C:23]([OH:25])=[O:24])([CH2:18][C:19]([OH:21])=[O:20])[C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 5360545Sodium2×HCID 21514905HCID 21514905, compound

Product 1

HCID 21514903HCID 21514903, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

4-Methoxy-10-oxo-9,10-dihydroanthracene-9,9-diacetic acid, whose preparation is described in Example 2, (5.2 g.) in n-butanol (300 ml.) is heated under reflux and sodium (10 g.) is gradually added in small pieces to the boiling solution. When all the sodium has dissolved, the solution is allowed to cool and is then extracted three times with water. The aqueous extracts are combined, washed with ether and acidified with concentrated hydrochloric acid. The resulting precipitate is extracted into ether, the ether is washed with water, dried (MgSO4) and evaporated to give a solid which is recrystallised from ethyl acetate-petroleum ether (b.p. 60°-80°C.) to give 4-methoxy-9,10-dihydroanthracene-9,9-diacetic acid m.p. 150°-153°C.

Workup

  1. temperatureis heated
  2. temperatureunder reflux
  3. temperatureto cool
  4. extractionis then extracted three times with water
  5. washwashed with ether
  6. extractionThe resulting precipitate is extracted into ether
  7. washthe ether is washed with water
  8. dry with materialdried (MgSO4)
  9. customevaporated
  10. customto give a solid which
  11. customis recrystallised from ethyl acetate-petroleum ether (b.p. 60°-80°C.)

Sources & evidence

ORD record
ord-93e0a77fc29f47b292398a394926bb31
Source dataset
uspto-grants-1976_09
Patent number
US03979513

Reaction notes

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