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Synthesis of 4-(Methylthio)benzeneacetic Acid

Yinhua Huang, Jin Ningren

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Abstract

As an intermediate for COX-2 inhibiters,4-(methylthio)benzeneacetic acid(Ⅳ) was prepared via Friedel-Crafts and Willgerodt-Kindler reaction from thioanisole(Ⅰ).When the molar ratio of Ⅰ to acetyl chloride and AlCl_3 was 1∶1.1∶1.3 and CS_2 was used as solvent,after reacting at(0°C) for 6 h the yield of 4-(methylthio) acetophenone(Ⅱ) was 75.9%.Ⅱ was refluxed 5 h with morpholine and sulfur to give thioacetmorpholide(Ⅲ),then Ⅲ was refluxed in 10% NaOH for 10 h to give Ⅳ with an overall yield of 63.5% and purity of 99.0%(by HPLC).The structure was confirmed by IR and()~1H NMR.

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What this paper is about

As an intermediate for COX-2 inhibiters,4-(methylthio)benzeneacetic acid(Ⅳ) was prepared via Friedel-Crafts and Willgerodt-Kindler reaction from thioanisole(Ⅰ).When the molar ratio of Ⅰ to acetyl chloride and AlCl_3 was 1∶1.1∶1.3 and CS_2 was used as solvent,after reacting at(0°C) for 6 h the yield of 4-(methylthio) acetophenone(Ⅱ) was 75.9%.Ⅱ was refluxed 5 h with morpholine and sulfur to give thioacetmorpholide(Ⅲ),then Ⅲ was refluxed in 10% NaOH for 10 h to give Ⅳ with an overall yield of 63.5% and purity of 99.0%(by HPLC).The structure was confirmed by IR and()~1H NMR.

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Available abstract

As an intermediate for COX-2 inhibiters,4-(methylthio)benzeneacetic acid(Ⅳ) was prepared via Friedel-Crafts and Willgerodt-Kindler reaction from thioanisole(Ⅰ).When the molar ratio of Ⅰ to acetyl chloride and AlCl_3 was 1∶1.1∶1.3 and CS_2 was used as solvent,after reacting at(0°C) for 6 h the yield of 4-(methylthio) acetophenone(Ⅱ) was 75.9%.Ⅱ was refluxed 5 h with morpholine and sulfur to give thioacetmorpholide(Ⅲ),then Ⅲ was refluxed in 10% NaOH for 10 h to give Ⅳ with an overall yield of 63.5% and purity of 99.0%(by HPLC).The structure was confirmed by IR and()~1H NMR.

Key concepts: Chemistry, Yield (engineering), Acetophenone, Thioanisole, Morpholine, Molar ratio, Sulfur, Solvent

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