Methanol → Anthraquinone

HRID 258360Notes

Reaction equation

HRID 258360 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](Br)=[CH:4][C:3]=1C(O)=O.OCCS(C1C=CC(OC2C=CC(S)=CC=2)=CC=1)(=O)=O.C(=O)([O-])[O-].[K+].[K+].CO>C1C=C(Cl)C(Cl)=CC=1>[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

6

Reactant 4

HCID 887MethanolHCID 11430Potassium CarbonateHCID 2715931-Amino-4-bromo-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acidHCID 197376974-(4'-beta-Hydroxyethylsulfonylphenoxy)thiophenol

Product 1

HCID 6780Anthraquinone

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

1-Amino-2-carboxy-4-bromoanthraquinone (6.9 parts) and 4-(4'-β-hydroxyethylsulfonylphenoxy)thiophenol (6.5 parts) were allowed to react with each other at 100° to 120° C. in O-dichlorobenzene in the presence of cuprous chloride and potassium carbonate. Thereafter, methanol was added to the reaction mixture to deposit solids, which were collected on a filter, washed throughly with methanol and water and then dried at 80° C. The resulting product was subjected to sulfonation and esterification simultaneously at 20° to 40° C. in 14% oleum. Thereafter, ice was added thereto, and the solids deposited were collected on a filter, thereby obtaining an anthraquinone compound of the following formula (free acid form). ##STR383##

Workup

  1. customwere collected on a filter
  2. washwashed throughly with methanol and water
  3. customdried at 80° C
  4. customwas subjected to sulfonation and esterification simultaneously at 20° to 40° C. in 14% oleum
  5. additionThereafter, ice was added
  6. customthe solids deposited were collected on a filter

Sources & evidence

ORD record
ord-e3d1a3cf59a446d8a6a2d288aaaaf91e
Source dataset
uspto-grants-1993_11
Patent number
US05266696

Reaction notes

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