2015Journal of Jiangxi Normal UniversityRequires access

The One-Pot,Two-Step Synthesis of Several Biphenols Containing Cyclohexyl Groups

YU Lame

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Abstract

An improved one-pot,two-step process of synthesis of five kinds of biphenols containing cyclohexyl groups such as 1,1-bis( 4-hydroxyphenyl) cyclohexane,1,1-bis( 4-hydroxy-3-methyphenyl) cyclohexane,1,1-bis( 4-hydroxy-3,5-dimethyphenyl) cyclohexane,1,1-bis( 4-hydroxyphenyl)-4-methylcyclohexane and 1,1-bis-( 4-hydroxyphenyl)-4-tert-butylcyclohexane in 82. 5%-86. 0% yields was developed through chlorination reaction of cyclohexanone,4-methylcyclohexanone and 4-tert-butyl cyclohexanone with thionyl chloride,affording the intermediate 4,4-cyclohexanone or its derivatives without further isolation and purification,followed by treatment with phenol,o-cresol and 2,6-dimethylphenol,respectively. Their structures were characterized by elemental analysis,FT-IR,1H NMR and 13 C NMR spectra. The present method has advantages such as mild reaction condition,convenient manipulation and good yield.

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An improved one-pot,two-step process of synthesis of five kinds of biphenols containing cyclohexyl groups such as 1,1-bis( 4-hydroxyphenyl) cyclohexane,1,1-bis( 4-hydroxy-3-methyphenyl) cyclohexane,1,1-bis( 4-hydroxy-3,5-dimethyphenyl) cyclohexane,1,1-bis( 4-hydroxyphenyl)-4-methylcyclohexane and 1,1-bis-( 4-hydroxyphenyl)-4-tert-butylcyclohexane in 82. 5%-86. 0% yields was developed through chlorination reaction of cyclohexanone,4-methylcyclohexanone and 4-tert-butyl cyclohexanone with thionyl chloride,affording the intermediate 4,4-cyclohexanone or its derivatives without further isolation and purification,followed by treatment with phenol,o-cresol and 2,6-dimethylphenol,respectively. Their structures were characterized by elemental analysis,FT-IR,1H NMR and 13 C NMR spectra. The present method has advantages such as mild reaction condition,convenient manipulation and good yield.

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Available abstract

An improved one-pot,two-step process of synthesis of five kinds of biphenols containing cyclohexyl groups such as 1,1-bis( 4-hydroxyphenyl) cyclohexane,1,1-bis( 4-hydroxy-3-methyphenyl) cyclohexane,1,1-bis( 4-hydroxy-3,5-dimethyphenyl) cyclohexane,1,1-bis( 4-hydroxyphenyl)-4-methylcyclohexane and 1,1-bis-( 4-hydroxyphenyl)-4-tert-butylcyclohexane in 82. 5%-86. 0% yields was developed through chlorination reaction of cyclohexanone,4-methylcyclohexanone and 4-tert-butyl cyclohexanone with thionyl chloride,affording the intermediate 4,4-cyclohexanone or its derivatives without further isolation and purification,followed by treatment with phenol,o-cresol and 2,6-dimethylphenol,respectively. Their structures were characterized by elemental analysis,FT-IR,1H NMR and 13 C NMR spectra. The present method has advantages such as mild reaction condition,convenient manipulation and good yield.

Key concepts: Cyclohexanone, Chemistry, Cyclohexane, Yield (engineering), One-pot synthesis, Phenol, Proton NMR, Methylcyclohexane

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