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Article Dans Une Revue Reaction Chemistry & Engineering Année : 2022

Efficient Piancatelli rearrangement on a large scale using the Zippertex technology under subcritical water conditions

Résumé

Piancatelli rearrangement of furyl carbinols is a relevant reaction to produce cyclopentenone derivatives. However, on large scale, Piancatelli rearrangement suffers several serious drawbacks such as long reaction period, high dilution conditions, moderate yields and the formation of dark brown polymeric materials. We described here the first use of Zippertex, an innovative technology reaching the subcritical water conditions (100-150 °C and 100 bars). In these conditions, this rearrangement proceeds smoothly to provide clean crude reaction mixtures without the formation of side-products and dark brown polymeric materials. Thus, a series of simple furyl carbinols directly obtained from bio-sourced furfural, and more challenging non-symmetrical furan-2,5-dicarbinol substrates, also obtained from bio-sourced raw material (HMF), were efficiently transformed into cyclopentenone derivatives in good yields. This technology could be applied successfully on challenging substrates substituted by an aliphatic group and also performed on 500 mmol scale.logy under subcritical water conditions.

Domaines

Chimie organique
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Dates et versions

hal-03767361 , version 1 (01-09-2022)

Identifiants

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Guillaume Arcile, Jamal Ouazzani, Jean-François Betzer. Efficient Piancatelli rearrangement on a large scale using the Zippertex technology under subcritical water conditions. Reaction Chemistry & Engineering, 2022, 7 (7), pp.1640-1649. ⟨10.1039/D2RE00098A⟩. ⟨hal-03767361⟩
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