著者

佐方 易忠 橋本 忠

出版者

公益社団法人 日本薬学会

雑誌

藥學雜誌 (ISSN:00316903)

巻号頁・発行日

vol.79, no.7, pp.878-880, 1959

被引用文献数

3

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In order to examine chemical properties of <i>p</i>-trimethylsilylphenol (I), reaction of (I) with several kinds of cationoid reagents was carried out. Application of bromine to (I) affords <i>p</i>-bromophenol, while that of benzenediazonium chloride gives 4-hydroxyazobenzene. Nitration of acetate (II) of (I) with acetyl nitrate affords <i>p</i>-nitrophenyl acetate and the Friedel-Crafts reaction of the methyl ether (III) of (I) with anhydrous aluminum chloride and acetic anhydride gives <i>p</i>-methoxyacetophenone. The Fries rearrangement of (II) results in formation of <i>o</i>- and <i>p</i>-hydroxyacetophenone. The Reimer-Tiemann reaction of (I) affords 5-trimethyl-silylsalicylaldehyde. (I) is decomposed by 10% hydrochloric acid to form phenol but remains unchanged with 10% sodium hydroxide. These experimental results indicate that the cationoid reagents that easily undergo substitution at a position <i>para</i> to hydroxyl replaces the trimethylsilyl group in (I) while reagents that undergoes substitution in the <i>ortho</i> position does so in (I) without severance of a bond between silicon and the aromatic ring.