Water → 2-[(Oxiran-2-yl)methoxy]anthracene-9,10-dione

HRID 542398

Reaction equation

HRID 542398 reaction equation
[OH:1][C:2]1[CH:15]=[CH:14][C:13]2[C:12](=[O:16])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5](=[O:17])[C:4]=2[CH:3]=1.[H-].[Na+].[CH2:20]([CH:22]1[O:24][CH2:23]1)Cl.O>CN1CCCC1=O>[CH2:20]([O:1][C:2]1[CH:15]=[CH:14][C:13]2[C:12](=[O:16])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5](=[O:17])[C:4]=2[CH:3]=1)[CH:22]1[O:24][CH2:23]1

Participants

6

Reactant 4

HCID 962WaterHCID 7835EpichlorohydrinHCID 117962-HydroxyanthraquinoneHCID 24758Sodium hydride

Product 1

HCID 134236012-[(Oxiran-2-yl)methoxy]anthracene-9,10-dioneYield 50.57%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
0 °C

Procedure

112.1 g (0.5 mole) of 2-hydroxyanthraquinone are dissolved in 500 ml of N-methylpyrrolidone, and 12 g (0.5 mole) of sodium hydride are added in portions. When the evolution of gas has ended, 46.37 ml (0.5 mole) of epichlorohydrin are added dropwise at 70° C. and stirring is continued at 70° C. for a further 8 hours. 1.5 liters of water are then added, the mixture is filtered and the filter cake is dried in vacuo. After drying, the product is boiled up again in 1 liter of N,N-dimethylformamide with 10 g of active charcoal and filtered hot. The crystals which precipitate on cooling to 0° C. are separated off by filtration and dried under a high vacuum. 69.45 g (50.57% of theory) of 2-anthraquinonyl glycidyl ether are obtained; melting point: 162°-167° C.

Workup

  1. filtrationthe mixture is filtered
  2. customthe filter cake is dried in vacuo
  3. customAfter drying
  4. filtrationfiltered hot
  5. customThe crystals which precipitate
  6. customare separated off by filtration
  7. customdried under a high vacuum

Sources & evidence

ORD record
ord-f1f5d4946bec4e9abeb9250e65294a87
Source dataset
uspto-grants-1987_04
Patent number
US04657842

Linked notes

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