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Issue 5, 2002
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Mild catalytic multiphase hydrogenolysis of benzyl ethers

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Abstract

A preliminary study was conducted on the multiphase (aqueous KOH–isooctane–Aliquat® 336) hydrogenolysis of benzyl methyl ether using Pd/C, Pt/C and Raney-Ni as catalysts, under mild conditions (T = 50 °C, pH2 = 1 atm). Using ethanol as solvent, the Pd/C system is very efficient, while the same catalyst under multiphase conditions is almost inactive. With Pt/C, the reaction is always sluggish, and ring hydrogenation kicks in under multiphase conditions. The Raney-Ni system has an opposite behavior, while debenzylation is slow in ethanol, under multiphase conditions the reaction is quite fast. Other O-benzyl protected substrates undergo debenzylation with Raney-Ni as well, with varying chemoselectivity.

Graphical abstract: Mild catalytic multiphase hydrogenolysis of benzyl ethers

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Article information


Submitted
12 Jul 2002
First published
25 Sep 2002

Green Chem., 2002,4, 492-494
Article type
Paper

Mild catalytic multiphase hydrogenolysis of benzyl ethers

A. Perosa, P. Tundo and S. Zinovyev, Green Chem., 2002, 4, 492
DOI: 10.1039/B206838A

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