Methyl Ethyl Ketone → 1,4-Diethoxyanthracene-9,10-dione

HRID 899029Notes

Reaction equation

HRID 899029 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]2[C:15](=[O:16])[C:14]3[C:9](=[C:10]([OH:18])[CH:11]=[CH:12][C:13]=3[OH:17])[C:7](=[O:8])[C:5]=2[CH:6]=1.C(=O)([O-])[O-].[K+].[K+].S([O-])(O[CH2:29][CH3:30])(=O)=O.[CH2:32](C(C)=O)[CH3:33]>>[CH2:32]([O:18][C:10]1[C:9]2[C:7](=[O:8])[C:5]3[C:4](=[CH:3][CH:2]=[CH:1][CH:6]=3)[C:15](=[O:16])[C:14]=2[C:13]([O:17][CH2:29][CH3:30])=[CH:12][CH:11]=1)[CH3:33]

Participants

5

Reactant 4

HCID 6569Methyl Ethyl KetoneHCID 6688QuinizarinHCID 11430Potassium CarbonateHCID 3804841Ethyl sulfate anion

Product 1

HCID 2913671,4-Diethoxyanthracene-9,10-dione

Procedure

A mixture of quinizarin (20.0 g, 83.5 mmol), potassium carbonate (76 g, 550 mmol) and ethyl sulfate (38.6 g, 250 mmol) was refluxed in methyl ethyl ketone (MEK, 950 mL) for 24 hrs. The reaction was filtered hot through Celite using additional hot MEK. The solution was evaporated on a rotary evaporator until crystallization began, then the reaction was allowed to sit overnight. After cooling in an ice bath, the crystals were filtered, rinsed with Et2O, sucked dry, then dried overnight in a vacuum oven at 70° C. The yield was 14.0 g (57%) of yellow/orange crystals.

Workup

  1. filtrationThe reaction was filtered hot through Celite
  2. customThe solution was evaporated on a rotary evaporator until crystallization
  3. temperatureAfter cooling in an ice bath
  4. filtrationthe crystals were filtered
  5. washrinsed with Et2O
  6. customsucked dry
  7. customdried overnight in a vacuum oven at 70° C

Sources & evidence

ORD record
ord-d5f888cfda584a3db69b319b7bb9cb3e
Source dataset
uspto-grants-2008_04
Patent number
US07354692B2

Reaction notes

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