2018) 'Flow synthesis of coumalic acid and its derivatization.', Reaction chemistry engineering., 3 (5). pp. 722-732.The full-text may be used and/or reproduced, and given to third parties in any format or medium, without prior permission or charge, for personal research or study, educational, or not-for-prot purposes provided that:• a full bibliographic reference is made to the original source • a link is made to the metadata record in DRO • the full-text is not changed in any way The full-text must not be sold in any format or medium without the formal permission of the copyright holders.Please consult the full DRO policy for further details.Coumalic acid is a valuable platform compound which can be prepared from malic acid, a biorenewable feedstock readily derived from the fermentation of glucose. Current batch procedures to synthesise coumalic acid have several drawbacks, which we address with the aid of tubular flow systems and a simple heated rotating flow reactor. The prepared coumalate derivatives can be further used in inverse electron demand Diels-Alder reactions to synthesise compounds with many applications including molecular electronics, with the added advantage of providing metal-free preparations.
Historical context: syntheses of coumalic acid and derivativesThe earliest documented synthesis of coumalic acid was published by von Pechmann in 1891 starting from malic acid. 14 A mixture of concentrated sulfuric acid (97-98%) and fuming sulfuric acid was used at 70 °C to effect conversion to coumalic acid, in a reported 70% yield. Caldwell et al. reproduced the a.