The Prins Reaction in the Fragrance Industry: 100th Anniversary (1919–2019)

Abstract

The Prins reaction, an acid‐catalyzed condensation of alkenes with aldehydes, is used extensively in the fragrance industry. This year we celebrate the 100th anniversary of the discovery of this reaction. In honor of this occasion we present an overview of the diverse applications of the Prins reaction in the synthesis of flavor and fragrance ingredients. To pay tribute to the inventor of the Prins reaction, Hendrik Jacobus Prins, we also provide some insight into his life, scientific, and entrepreneurial accomplishments.

Florol synthesis via Prins cyclization over hierarchical beta zeolites

“…The catalytic performance of the prepared hierarchical zeolite catalysts was studied in the Prins cyclization reaction between biomass-derived isoprenol and isovaleraldehyde resulting in a commercial perfume ingredient (Florol®) [19,20]. Besides the desired tetrahydropyranol (THP), this reaction can also give several dehydration products (DHP) (Scheme 1) capable of subsequent reactions with the initial substrates (IVA or IP) resulting in trimers.…”