Potassium Hydroxide → 2-(3,6-Dihydroxyxanthen-9-yl)benzoic acid, potassium salt

HRID 1879619Notes

Reaction equation

HRID 1879619 reaction equation
[OH-].[K+:2].[OH:3][C:4]1[CH:5]=[CH:6][C:7]2[CH:8]([C:19]3[CH:27]=[CH:26][CH:25]=[CH:24][C:20]=3[C:21]([OH:23])=[O:22])[C:9]3[C:14]([O:15][C:16]=2[CH:17]=1)=[CH:13][C:12]([OH:18])=[CH:11][CH:10]=3>C(O)C>[OH:18][C:12]1[CH:11]=[CH:10][C:9]2[CH:8]([C:19]3[CH:27]=[CH:26][CH:25]=[CH:24][C:20]=3[C:21]([O-:23])=[O:22])[C:7]3[C:16]([O:15][C:14]=2[CH:13]=1)=[CH:17][C:4]([OH:3])=[CH:5][CH:6]=3.[K+:2]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 68205Benzoic acid, 2-(3,6-dihydroxy-9H-xanthen-9-yl)-

Product 1

HCID 441521022-(3,6-Dihydroxyxanthen-9-yl)benzoic acid, potassium saltYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Aqueous potassium hydroxide (1 mL of 0.1 N, 0.1 mmol) was added to a solution of 2-(3,6-dihydroxy-9H-xanthen-9-yl)-benzoic acid [33 mg, 0.1 mmol, Cui, Y. et al., Yaoxue Tongbao, 1982, 17(9), 528] in 5 mL of ethanol and the mixture was stirred for additional 2 h at room temperature. The mixture was evaporated to dryness under reduced pressure to give 37 mg (100% yield) of the desired compound as a orange solid, mp>300° C. 1H NMR (D2O, 300 MHz): δ5.76 [s, H, —CH], 6.94-6.99 [m, 1H, Ar—H], 7.09-7.13 [m, 2H, Ar—H], 7.26-7.31 [m, 6H, Ar—H], 7.49-7.54 [m, 1H, Ar—H].

Workup

  1. customThe mixture was evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-0247b0d702824cb483de27912faa5257
Source dataset
uspto-grants-2012_11
Patent number
US08318699B2

Reaction notes

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