Methanol → Anthraquinone

HRID 258353Notes

Reaction equation

HRID 258353 reaction equation
N[C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:17])[C:6]=2[C:5](SC2C=CC=C(S(CCO)(=O)=O)C=2)=[CH:4][C:3]=1Br.C1(O)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].CO>CN(C)C=O.OS(O)(=O)=O.O=S(=O)=O>[CH:9]1[C:8]2[C:7](=[O:17])[C:6]3[C:15](=[CH:2][CH:3]=[CH:4][CH:5]=3)[C:14](=[O:16])[C:13]=2[CH:12]=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 996PhenolHCID 11430Potassium CarbonateHCID 19737676HCID 19737676, compound

Product 1

HCID 6780Anthraquinone

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 24681Fuming sulfuric acidSolvent

Procedure

1-Amino-2-bromo-4-(3'-β-hydroxyethylsulfonylphenylthio)anthraquinone (5.2 parts) and phenol (9.5 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 thereto to deposit crystals, which were 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. Thereafter, ice was added to the reaction mixture to deposit crystals, which were collected on a filter to obtain an anthraquinone compound of the following formula (free acid form). ##STR197##

Workup

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

Sources & evidence

ORD record
ord-c652d3274cea43919805a902fe2e49db
Source dataset
uspto-grants-1993_11
Patent number
US05266696

Reaction notes

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