화학공학소재연구정보센터
Chemistry Letters, Vol.34, No.2, 188-189, 2005
A practical synthesis and estrogenic activity of 5-hydroxy-1-(4'-hydroxyphenyl)-1,3,3-trimethylindan, a contaminant in industrial grade bisphenol A
A practical synthesis of 5-hydroxy-1-(4'-hydroxyphenyl)1,3,3-trimethylindan was achieved from alpha-methylstyrene. The starting compound was dimerized in the presence of trifluoroacetic acid to produce 1-phenyl-1,3,3-trimethylindan. Aromatic nitration of the phenylindane was carried out using a mixture of nitric acid and acetic anhydride. The nitro group was then converted to hydroxyl via reduction and a diazonium salt sequence to form 5-hydroxy-1-(4'-hydroxyphenyl)-1,3,3-trimethylindan. The estrogenicity of the product was 8.7 times that of BPA. Our finding has demonstrated the endocrine-disrupting properties of the product.