Abstract
Our previous work established a continuous-flow synthesis of pristane, which is a saturated branched alkane obtained from a Basking Shark. The dehydration of an allylic alcohol that is the key to a tetraene was carried out using a packed-bed reactor charged by an acid–silica catalyst (HO-SAS) and flow hydrogenation using molecular hydrogen via a Pd/C catalyst followed. The present work relies on the additional propensity of Pd/C to serve as an acid catalyst, which allows us to perform a flow synthesis of pristane from the aforementioned key allylic alcohol in the presence of molecular hydrogen using Pd/C as a single catalyst, which is applied to both dehydration and hydrogenation. The present one-column-two-reaction-flow system could eliminate the use of an acid catalyst such as HO-SAS and lead to a significant simplification of the production process.
Highlights
IntroductionPublisher’s Note: MDPI stays neutral with regard to jurisdictional claims in published maps and institutional affiliations
The resultant tetraene 2 can be reduced to pristane 3 in a batch flask using molecular hydrogen with Pd on carbon (Pd/C) as the catalyst [6]
We are pleased to report a simple protocol for the flow synthesis of pristane using Pd/C as a single catalyst in a dual function, which avoids the need to use an acid catalyst
Summary
Publisher’s Note: MDPI stays neutral with regard to jurisdictional claims in published maps and institutional affiliations. Since Pd/C often causes dehydrative hydrogenation of allylic alcohols [12,13,14,15,16,17], we were curious as to whether pristane 3 could be synthesized using only a Pd/C catalyst. In this communication, we are pleased to report a simple protocol for the flow synthesis of pristane using Pd/C as a single catalyst in a dual function, which avoids the need to use an acid catalyst.
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