2-Mercaptobenzoic Acid → 1,5-Bis(o-carboxyphenylthio)anthraquinone

HRID 904886Notes

Reaction equation

HRID 904886 reaction equation
Cl[C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[C:9](Cl)[CH:10]=[CH:11][CH:12]=3)[C:7](=[O:18])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[SH:19][C:20]1[CH:28]=[CH:27][CH:26]=[CH:25][C:21]=1[C:22]([OH:24])=[O:23].[C:29](=[O:32])([O-])[O-:30].[K+].[K+].CN(C)C=O>C(O)(=O)C.O>[C:22]([C:21]1[CH:25]=[CH:26][CH:27]=[CH:28][C:20]=1[S:19][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[C:9]([S:19][C:20]4[CH:28]=[CH:27][CH:26]=[CH:25][C:21]=4[C:29]([OH:30])=[O:32])[CH:10]=[CH:11][CH:12]=3)[C:7](=[O:18])[C:6]=2[CH:5]=[CH:4][CH:3]=1)([OH:24])=[O:23]

Participants

7

Reactant 4

HCID 54432-Mercaptobenzoic AcidHCID 6228DimethylformamideHCID 67111,5-DichloroanthraquinoneHCID 11430Potassium Carbonate

Product 1

HCID 30860581,5-Bis(o-carboxyphenylthio)anthraquinone

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of 1,5-dichloroanthraquinone (13.8 grams, 0.05 mole), o-mercapto benzoic acid (15.4 grams, 0.10 mole), potassium carbonate (13.8 grams, 0.10 mole), and N,N-dimethylformamide (200 ml) was heated at approximately 125° C. for four hours. The reaction mixture was allowed to cool to room temperature and then drowned into water (500 ml) and acidified with acetic acid to a pH of about 5.0. The dye was collected by filtration, washed with hot water, and then dried in air to yield 23.5 grams of yellow dye.

Workup

  1. temperatureto cool to room temperature
  2. filtrationThe dye was collected by filtration
  3. washwashed with hot water
  4. customdried in air
  5. customto yield 23.5 grams of yellow dye

Sources & evidence

ORD record
ord-ad2b4fb8e9704d5183f8ebc8a4f61a4b
Source dataset
uspto-grants-1983_12
Patent number
US04420581

Reaction notes

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