Hydrolysis of Diazonium Salts Using a Two-Phase System (CPME and Water)
Corresponding Author
Toshihide Taniguchi
Seika Corporation, Wakayama, 641-0007 Japan
Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, Sakai, Osaka, 599-8531 Japan
Correspondence to: Toshihide Taniguchi; e-mail: [email protected].Search for more papers by this authorTakeo Nakai
Osaka Municipal Technical Research Institute, Joto-ku, Osaka, 536–8553 Japan
Search for more papers by this authorMasatoshi Mihara
Osaka Municipal Technical Research Institute, Joto-ku, Osaka, 536–8553 Japan
Search for more papers by this authorToshiyuki Iwai
Osaka Municipal Technical Research Institute, Joto-ku, Osaka, 536–8553 Japan
Search for more papers by this authorTakatoshi Ito
Osaka Municipal Technical Research Institute, Joto-ku, Osaka, 536–8553 Japan
Search for more papers by this authorTakumi Mizuno
Osaka Municipal Technical Research Institute, Joto-ku, Osaka, 536–8553 Japan
Search for more papers by this authorAkihiro Nomoto
Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, Sakai, Osaka, 599-8531 Japan
Search for more papers by this authorAkiya Ogawa
Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, Sakai, Osaka, 599-8531 Japan
Search for more papers by this authorCorresponding Author
Toshihide Taniguchi
Seika Corporation, Wakayama, 641-0007 Japan
Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, Sakai, Osaka, 599-8531 Japan
Correspondence to: Toshihide Taniguchi; e-mail: [email protected].Search for more papers by this authorTakeo Nakai
Osaka Municipal Technical Research Institute, Joto-ku, Osaka, 536–8553 Japan
Search for more papers by this authorMasatoshi Mihara
Osaka Municipal Technical Research Institute, Joto-ku, Osaka, 536–8553 Japan
Search for more papers by this authorToshiyuki Iwai
Osaka Municipal Technical Research Institute, Joto-ku, Osaka, 536–8553 Japan
Search for more papers by this authorTakatoshi Ito
Osaka Municipal Technical Research Institute, Joto-ku, Osaka, 536–8553 Japan
Search for more papers by this authorTakumi Mizuno
Osaka Municipal Technical Research Institute, Joto-ku, Osaka, 536–8553 Japan
Search for more papers by this authorAkihiro Nomoto
Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, Sakai, Osaka, 599-8531 Japan
Search for more papers by this authorAkiya Ogawa
Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, Sakai, Osaka, 599-8531 Japan
Search for more papers by this authorABSTRACT
A new method for the hydrolysis of diazonium salts, without the formation of tar, was developed. A two-phase system consisting of cyclopentyl methyl ether (CPME) and water is very effective for the hydrolysis of diazonium salts. Using this solvent system, the diazonium salt prepared from 3-(4-nitrophenoxy)aniline gave 3-(4-nitrophenoxy)phenol in high yield (96%) within 20 min. The synthesized phenol is an industrially important raw material in polymer syntheses. Furthermore, the use of the present two-phase system of CPME and water successfully brought about the efficient conversions of several m-substituted anilines into the corresponding m-substituted phenols. This is the first example of hydrolysis of diazonium salts using the two-phase system (CPME and water).
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