Sustainable Syntheses of Paracetamol and Ibuprofen from Biorenewable beta-pinene

Scalable processes have been developed to convert beta-pinene into 4-isopropenylcyclohexanone, which is then used as a feedstock for the divergent synthesis of sustainable versions of the common painkillers, paracetamol and ibuprofen. Both synthetic routes use Pd-0 catalysed reactions to aromatize the cyclohexenyl rings of key intermediates to produce the benzenoid ring systems of both drugs. The potential of using bioderived 4-hydroxyacetophenone as a drop-in feedstock replacement to produce sustainable aromatic products is also discussed within a terpene biorefinery context.

Automated summary

Scalable processes have been developed to convert beta-pinene into 4-isopropenylcyclohexanone, which is then used as a feedstock for the divergent synthesis of sustainable versions of paracetamol and ibuprofen. The use of bioderived 4-hydroxyacetophenone as a replacement feedstock for sustainable aromatic products is also discussed within a terpene biorefinery context.