Abstract
A biomass-based route to the preparation of hydroquinone starting from the renewable starting material quinic acid is described. Amberlyst-15 in the dry form promoted the one-step formation of hydroquinone from quinic acid in toluene without any oxidants or metal catalysts in 72 % yield. Several acidic polymer-based resins and organic acids as promoters as well as a variety of reaction conditions were screened including temperature, concentration and low- and high-boiling-point solvents. A 1:4 (w/w) ratio of quinic acid/Amberlyst-15 was determined to be optimal to promote hydroquinone formation with only traces of a dimeric side-product. A mechanism has been proposed based on the decarbonylation of protonated quino-1,5-lactone that is supported by experimental and computational calculation data.
| Original language | English |
|---|---|
| Pages (from-to) | 3856-3861 |
| Number of pages | 6 |
| Journal | European Journal of Organic Chemistry |
| Volume | 2016 |
| Issue number | 22 |
| DOIs | |
| Publication status | Published - 2016 |
| Publication type | A1 Journal article-refereed |
Publication forum classification
- Publication forum level 1
Access to Document
- eujoc
This is the pre-peer reviewed version of the following article: Assoah, B., Veiros, L. F., Afonso, C. A. M. and Candeias, N. R. (2016), Biomass-Based and Oxidant-Free Preparation of Hydroquinone from Quinic Acid. Eur. J. Org. Chem., 2016: 3856–3861., which has been published in final form at 10.1002/ejoc.201600616.