2,4-DIHYDROXYBENZOYLTETRACHLORO-o-BENZOIC ACID AND 2,3,4-TRICHLORO-6-HYDROXYXANTHONE-1-CARBOXYLIC ACID AND SOME OF THEIR DERIVATIVES.

Orndorff, W. R.; Adamson, W. A.

doi:10.1021/ja02241a014

Cited by 4 publications

(6 citation statements)

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“…Bromination of HBBA using Br 2 and hot glacial acetic acid to prepare dibrominated 3,5diBrHBBA was previously reported [40]. Using the same method but with half the amount of Br 2 , a mixture that consisted of the monobrominated 5BrHBBA (~74%) and the dibrominated compound (~20%) was obtained in the present work.…”

Section: Resultsmentioning

confidence: 58%

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Preparation of two novel monobrominated 2-(2′,4′-dihydroxybenzoyl)-3,4,5,6-tetrachlorobenzoic acids and their separation from crude synthetic mixtures using vortex counter-current chromatography

Weisz

Witten

Zhang

et al. 2012

Journal of Chromatography A

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The present work describes the preparation of two compounds considered to be likely precursors of an impurity present in samples of the color additives D&C Red No. 27 (Colour Index 45410:1) and D&C Red No. 28 (Colour Index 45410, phloxine B) submitted to the U.S. Food and Drug Administration for batch certification. The two compounds, 2-(2′,4′-dihydroxy-3′-bromobenzoyl)-3,4,5,6-tetrachlorobenzoic acid (3BrHBBA) and its 5′-brominated positional isomer (5BrHBBA), both not reported previously, were separated from synthetic mixtures by vortex counter-current chromatography (VCCC). 3BrHBBA was prepared by chemoselective ortho-bromination of the dihydroxybenzoyl moiety. Two portions of the obtained synthetic mixture, 200 mg and 210 mg, respectively, were separated by VCCC using two two-phase solvent systems that consisted of hexane-ethyl acetate-methanol-aqueous 0.2% trifluoroacetic acid (TFA) in the volume ratios of 8:2:5:5 and 7:3:5:5, respectively. These separations produced 35 mg and 78 mg of 3BrHBBA, respectively, each product of over 98% purity by HPLC at 254 nm. 5BrHBBA was prepared by monobromination of the dihydroxybenzoyl moiety in the presence of glacial acetic acid. To separate the obtained synthetic mixture, VCCC was performed in the pH-zone-refining mode with a solvent system consisting of hexane-ethyl acetate-methanol-water (6:4:5:5, v/v) and with TFA used as the retainer acid and aqueous ammonia as the eluent base. Separation of a 1-g mixture under these conditions resulted in 142 mg of 5BrHBBA of ~99% purity by HPLC at 254 nm. The isolated compounds were characterized by high-resolution mass spectrometry and proton nuclear magnetic resonance spectroscopy.

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Section: Resultsmentioning

confidence: 58%

“…The synthetic mixture of 5BrHBBA used in this work was prepared by bromination of HBBA, using half as much bromine as that reported for the preparation of the dibrominated compound 3,5diBrHBBA [40]. Thus, HBBA (2.04 g, 5.18 mmol) and hot glacial acetic acid (15 ml) were placed in a 200-ml round-bottomed flask equipped with a magnetic stirbar.…”

Section: Methodsmentioning

confidence: 99%

Preparation of two novel monobrominated 2-(2′,4′-dihydroxybenzoyl)-3,4,5,6-tetrachlorobenzoic acids and their separation from crude synthetic mixtures using vortex counter-current chromatography

Weisz

Witten

Zhang

et al. 2012

Journal of Chromatography A

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“…The title compound, (I), is an intermediate in the synthesis of fluorescein and was first prepared by Baeyer (1876) and also by Bollmann (1922) in his study of resorcinbenzein. Further details about the title compound and its derivatives have been reported (Orndorff & Adamson, 1918;Orndorff & Kelley, 1922Orndorff & Kline, 1924. Despite extensive investigations with repect to its synthesis, there has not been a crystallographic study of (I).…”

Section: Commentmentioning

confidence: 99%

2-(2,4-Dihydroxybenzoyl)benzoic acid

Li¹,

Chen²,

Dong³

et al. 2005

Acta Cryst E

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“…Resorcinol, condensed with the anhydride, yielded tetrachlorofluorescein and tetrachloro-o-fluorescein (35,72,77). From this compound was obtained a Phloxine dye, tetrachloroeosin (8, 9, 72, 77), and the closely related Rose Bengal 3B (8, 9).…”

Section: Tetrachlorophthalimidementioning

confidence: 99%

“…The anhydride is claimed to react with m-hydroxydiphenylamine to form a dye substance of the fluoran type (32). With dimethylaminophenol there was formed tetramethyltetrachloro-rhodamic tetrachlorophthalate (72). The free tetrachlororhodamine is obtained by treatment with a base, and this readily forms the hydrochloride with hydrochloric acid.…”

Section: Tetrachlorophthalimidementioning

confidence: 99%

Reactions and Uses of Tetrachlorophthalic Anhydride

Lawlor¹

1947

Ind. Eng. Chem.

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2,4-DIHYDROXYBENZOYLTETRACHLORO-o-BENZOIC ACID AND 2,3,4-TRICHLORO-6-HYDROXYXANTHONE-1-CARBOXYLIC ACID AND SOME OF THEIR DERIVATIVES.

Abstract: I235 turning yellow on further heating, and a t 232' decomposes with partial sublimation, leaving a small amount of a black residue. Calc. for CsHeOsNa: N, zz.oo%. Found: N, 21.87. AUSTIN, TEXAS.

Cited by 4 publications

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Preparation of two novel monobrominated 2-(2′,4′-dihydroxybenzoyl)-3,4,5,6-tetrachlorobenzoic acids and their separation from crude synthetic mixtures using vortex counter-current chromatography

Preparation of two novel monobrominated 2-(2′,4′-dihydroxybenzoyl)-3,4,5,6-tetrachlorobenzoic acids and their separation from crude synthetic mixtures using vortex counter-current chromatography

2-(2,4-Dihydroxybenzoyl)benzoic acid

Reactions and Uses of Tetrachlorophthalic Anhydride

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