Skip to content

Research at St Andrews

Synthesis of pharmaceutical drugs from cardanol derived from cashew nut shell liquid

Research output: Contribution to journalArticle


Open Access permissions



Yiping Shi, Paul C. J. Kamer, David J. Cole-Hamilton

School/Research organisations


Cardanol from cashew nut shell liquid extracted from cashew nut shells was successfully converted into various useful pharmaceutical drugs, such as norfenefrine, rac-phenylephrine, etilefrine and fenoprofene. 3-Vinylphenol, the key intermediate for the synthesis of these drugs, was synthesised from cardanol by ethenolysis to 3-non-8-enylphenol followed by isomerising ethenolysis. The metathesis reaction worked very well using DCM, but the greener solvent, 2-methyl tetrahydrofuran, also gave very similar results. Hydroxyamination of 3-vinylphenol with an iron porphyrin catalyst afforded norfenefrine in over 70% yield. Methylation and ethylation of norfenefrine afforded rac-phenylephrine and etilefrine respectively. A sequence of C–O coupling, isomerising metathesis and selective methoxycarbonylation afforded fenoprofene in good yield. A comparison of the routes described in this paper with some standard literature syntheses of 3-vinylphenol and of the drug molecules shows significant environmental advantages in terms of precursors, yields, number of steps, conditions and the use of catalysts. The Atom Economy of our processes is generally similar or significantly superior to those of the literature processes mainly because the side products produced during synthesis of 3-vinylphenol (1-octeme, 1,4-cyclohexadiene and propene) are easily separable and of commercial value, especially as they are bio-derived. The E Factor for the production of 2-vinylphenol by our process is also very low compared with those of previously reported syntheses.


Original languageEnglish
Pages (from-to)1043-1053
Number of pages11
JournalGreen Chemistry
Issue number5
Publication statusPublished - 7 Mar 2019

Discover related content
Find related publications, people, projects and more using interactive charts.

View graph of relations

Related by author

  1. The role of chemists and chemical engineers in a sustainable world

    Cole-Hamilton, D. J., 11 Feb 2020, In : Chemistry - A European Journal. 26, 9, p. 1894-1899

    Research output: Contribution to journalArticle

  2. Periodic table: new version warns of elements that are endangered

    Cole-Hamilton, D., 24 Jan 2019, The Conversation.

    Research output: Contribution to specialist publicationArticle

  3. Employment and Careers of European Chemists (ESEC2)

    Salzer, R., Cole-Hamilton, D., Hrastelj, N. & Vilela, B., 20 Nov 2018, In : Chemistry - A European Journal. 24, 66, p. 17370-17388 19 p.

    Research output: Contribution to journalEditorial

  4. The European Chemical Society (EuChemS)

    Cole-Hamilton, D. J., 14 Aug 2018, In : Chemistry - A European Journal. 24, 46, p. 11811-11820

    Research output: Contribution to journalArticle

  5. Insight into the mechanism of decarbonylation of methanol by ruthenium complexes; a deuterium labelling study

    Lorusso, P., Eastham, G. & Cole-Hamilton, D. J., 15 Jun 2018, In : Dalton Transactions. In press

    Research output: Contribution to journalArticle

Related by journal

  1. Is oxidation-reduction a real robust strategy for lignin conversion? A comparative study on lignin and model compounds

    Guo, H., Miles-Barrett, D., Zhang, B., Wang, A-Q., Zhang, T., Westwood, N. J. & Li, C., 21 Feb 2019, In : Green Chemistry. 21, 4, p. 803-811

    Research output: Contribution to journalArticle

  2. Evaluating polymer-supported isothiourea catalysis in industrially-preferable solvents for the acylative kinetic resolution of secondary and tertiary heterocyclic alcohols in batch and flow

    Guha, N., Neyya Ppadath, R. M., Greenhalgh, M., Chisholm, R., Smith, S., McEvoy, M., Rodríguez-Escrich, C., Young, C. M., Pericas, M. A., Hähner, G. & Smith, A. D., 24 Aug 2018, In : Green Chemistry. In press

    Research output: Contribution to journalArticle

  3. Iridium-catalysed primary alcohol oxidation and hydrogen shuttling for the depolymerisation of lignin

    Lancefield, C. S., Teunissen, L. W., Weckhuysen, B. M. & Bruijnincx, P. C. A., 21 Jul 2018, In : Green Chemistry. 20, 14, p. 3214-3221 8 p.

    Research output: Contribution to journalArticle

  4. Microplasma-assisted electrochemical synthesis of Co3O4 nanoparticles in absolute ethanol for energy applications

    Ni, C., Carolan, D., Rocks, C., Hui, J., Fang, Z., Padmanaban, D. B., Ni, J-P., Xie, D., Maguire, P., Irvine, J. T. S. & Mariotti, D., 7 May 2018, In : Green Chemistry. 20, 9, p. 2101-2109 9 p.

    Research output: Contribution to journalArticle

ID: 258270851