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Communication | Special issue | Vol 76, No. 2, 2008, pp.1061-1067
Published online, 10th July, 2008
DOI: 10.3987/COM-08-S(N)111
Regioselective Mannich Reaction of Phenols under High Pressure Using Dichloromethane as C1 Unit

Kiyoshi Matsumoto,* Kouta Joho, Seisuke Mimori, Hirokazu Iida,* Hiroshi Hamana, and Akikazu Kakehi

*Faculty of Pharmacy, Chiba Institute of Science, Choshi, Chiba 288-0025 Japan


Regioselectivity in Mannich reaction of 4-, 3-, and 2-substituted phenols with typical heterocyclic amines are investigated under reaction conditions developed by us. Phenol and 4-alkyl, and 4-chlorophenols in the title reaction predominantly gave the corresponding 2-(aminomethyl)phenols, while 4- methoxyphenol afforded, in addition to the mono(aminomethyl)phenols, a considerable amount of the bis adducts. Peculiarly enough, 3-methylphenol with amines afforded 3-methyl-4-(aminomethyl)phenols whereas 2-methylphenol produced 2-methyl-6-(aminomethyl)phenols.