Methanol → Anthraquinone

HRID 258351Notes

Reaction equation

HRID 258351 reaction equation
N[C:2]1[C:15]2C(=S)[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:17])[C:6]=2[C:5]([C:18]2C=CC=CC=2)=[CH:4][C:3]=1Br.[OH:25]CCS(C1C=C(O)C=CC=1)(=O)=O.C(=O)([O-])[O-].[K+].[K+].CO>CN(C)C=O.OS(O)(=O)=O.O=S(=O)=O>[CH:12]1[C:13]2[C:18](=[O:25])[C:5]3[C:6](=[CH:15][CH:2]=[CH:3][CH:4]=3)[C:7](=[O:17])[C:8]=2[CH:9]=[CH:10][CH:11]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 11430Potassium CarbonateHCID 54060150HCID 54060150, compoundHCID 57064618HCID 57064618, compound

Product 1

HCID 6780Anthraquinone

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 24681Fuming sulfuric acidSolvent

Procedure

1-Amino-2-bromo-4-phenylthioanthraquinone (4.1 parts) and 3-β-hydroxyethylsulfonylphenol (2.1 parts) were allowed to react with each other at 100° to 120° C. in dimethylformamide in the presence of potassium carbonate. After completion of the reaction, methanol was added to the reaction mixture to deposit crystals, which were then collected on a filter, well washed with water and then dried at 80° C. The product obtained was subjected to both sulfonation and esterification at 20° to 40° C. in 10% oleum. Ice was added to the reaction mixture to deposit crystals, which were then collected on a filter to obtain an anthraquinone compound of the following formula (free acid form). ##STR182##

Workup

  1. additionwas added to the reaction mixture to deposit crystals, which
  2. customwere then collected on a filter
  3. washwell washed with water
  4. customdried at 80° C
  5. customThe product obtained
  6. additionIce was added to the reaction mixture to deposit crystals, which
  7. customwere then collected on
  8. filtrationa filter

Sources & evidence

ORD record
ord-e79a527c03914ea0b541dd1b794dee8a
Source dataset
uspto-grants-1993_11
Patent number
US05266696

Reaction notes

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