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Citation: FU Gui-Yun, WEI Wei-Hong, SHENG Shou-Ri, JIANG Jian-Wen. Synthesis of 9,9-Bis[4-(4-carboxyphenoxy) phenyl] xanthene[J]. Chinese Journal of Applied Chemistry, ;2010, 27(12): 1478-1480. doi: 10.3724/SP.J.1095.2010.00059 shu

Synthesis of 9,9-Bis[4-(4-carboxyphenoxy) phenyl] xanthene

Institute of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang 330022

Received Date: 25 January 2010
Revised Date: 10 May 2010

The synthetic method of a new aromatic diacid,9,9-bis[4-(4-carboxyphenoxy) phenyl]xanthene(4) was developed from the reaction of 9,9-bis(4-hydroxyphenyl) xanthene(1) with 4-methyl-1-iodobenzene(2) by means of the Ullmann coupling and oxidation reaction successively. The treatment of compound 1 with compound 2 in DMF in the presence of cuprous iodide/tetrabutylammonium bromide/potassium phosphate at reflux temperature for 24 h afforded 9,9-bis[4-(4-methylphenoxy) phenyl]xanthene(3) in 95% yield.The compound 3 was then oxidized to the corresponding aromatic,9,9-bis[4-(4-carboxyphenoxy) phenyl]xanthene(4) in 84% yield directly using oxygen in the presence of a catalytic amount of N-bromosuccinimde(NBS) under photoirradiation. The new diacid 4 was obtained in an overall yield of about 79.8%(based on compound 1). The structure of the target compound was characterized by ¹H NMR,¹³C NMR,IR and elemental analysis. The present method has the advantage of convenient availability of starting materials,mild reaction conditions,convenient manipulation and good yield.
- bis [(carboxyphenoxy) phenyl] xanthene,
- bis (hydroxyphenyl) xanthene,
- methyliodobenzene,
- Ullmann reaction,
- oxidation reaction
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