The continuous catalytic debenzylation of 1,4-Dibenzyloxybenzene with H-2 in THF expanded with high pressure CO2

Akien, Geoffrey R. and Legeay, Jean-Christophe and Wells, Andrew and Poliakoff, Martyn (2010) The continuous catalytic debenzylation of 1,4-Dibenzyloxybenzene with H-2 in THF expanded with high pressure CO2. Organic Process Research and Development, 14 (5). pp. 1202-1208. ISSN 1083-6160

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Abstract

The continuous debenzylation of 1,4-dibenzyloxybenzene (1a) with H-2 and supported Pd catalysts has been studied in high-pressure CO2 + tetrahydrofuran. A range of parameters and catalysts have been tested, with one of the most successful results giving 86% conversion and 86% selectivity to the monodebenzylated product, 1,4-(benzyloxy)phenol (2a). In the absence of CO2, the reaction was unselective with no formation of 2a. When complete debenzylation was required, the best catalyst was 5% Pd supported on Deloxan APII, giving quantitative yields of hydroquinone (3), the completely debenzylated product, at temperatures as low as 50 degrees C. This Deloxan-supported catalyst was also substantially active at only 30 degrees C.

Item Type:
Journal Article
Journal or Publication Title:
Organic Process Research and Development
Uncontrolled Keywords:
/dk/atira/pure/subjectarea/asjc/1600/1606
Subjects:
ID Code:
72448
Deposited By:
Deposited On:
22 Jan 2015 10:14
Refereed?:
Yes
Published?:
Published
Last Modified:
23 Jan 2020 02:28