Abstract
Cinnamic acids have been prepared in moderate to high yields by a new direct synthesis using aromatic aldehydes and aliphatic carboxylic acids, in the presence of boron tribromide as reagent, 4-dimethylaminopyridine (4-DMAP) and pyridine (Py) as bases and N-methyl-2-pyrolidinone (NMP) as solvent, at reflux (180-190°C) for 8-12 hours.
Highlights
Cinnamic acids compose a relatively large family of organic acids which appear to have antibacterial, antifungal and antiparasitical activities
In a typical experimental procedure [10], cinnamic acids can be prepared from aromatic aldehydes and aliphatic carboxylic anhydrides in the presence of bases, with sodium or potassium salts of the carboxylic acids corresponding to the anhydrides used in reactions as reagents
This hypothesis was confirmed by our experimental results obtained by reacting acetic acid and boron tribromide, whereupon triacetyl borate was produced in situ, the product being identical to that prepared from boric acid and acetic anhydride according to the literature [13]
Summary
Cinnamic acids compose a relatively large family of organic acids which appear to have antibacterial, antifungal and antiparasitical activities They are used in macromolecular synthesis as very important building blocks for various classes of polymers, having attractive properties, especially a high photoreactivity due to the presence, in the main or side chains, of the cinnamoyl group, well known as photoresponsive unit. Polymers containing cinnamoyl moieties are used in a wide range of applications in emerging fields such as advanced microelectronics [1], photolithography [2], non-linear-optical materials [3], integrated circuit technology [4] and photocurable coatings [5] For their use in perfume production, the food industry, pharmaceuticals, medicine and technical applications, cinnamic acids are synthesized on a commercial scale. We wish to report a protocol for a new direct route for cinnamic acid synthesis, starting from aromatic aldehydes and aliphatic carboxylic acids, in the presence of boron tribromide as reagent
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