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

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<mark>Journal publication date</mark>2010
<mark>Journal</mark>Organic Process Research and Development
Issue number5
Number of pages7
Pages (from-to)1202-1208
Publication StatusPublished
<mark>Original language</mark>English


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.