The base-free chemoselective ring opening of epoxides with carboxylic acids using [bmim]Br: a rapid entry into 1,2-diol mono-esters synthesis

Abstract

A facile and highly convenient base-free protocol for the chemoselective preparation of 1,2-diol mono-esters is described. In this method, the regioselective ring opening of epoxides with carboxylic acids in the presence of [bmim]Br furnishes the corresponding 1,2-diol mono-esters in excellent yields. This method is efficient for various structurally diverse epoxides and carboxylic acids and it can be efficiently applied for the scale up synthesis of 1,2-diol mono-esters in reasonable to good yields. [bmim]Br remarkably influences the reaction progress and acts as both solvent and catalyst in this protocol.

Revisiting the Mukaiyama-type epoxidation for the conversion of styrene into styrene carbonate in the presence of O2 and CO2

“…This has been reported especially in the presence of ionic liquids involving bromides. 34 However, using GC-MS analysis, we have not been able to detect the addition product of isobutyric acid onto styrene oxide.…”

Enzyme-inspired dry-powder polymeric catalyst for green and fast pharmaceutical manufacturing processes

“…Compound 6 was synthesized in one step from cholesteryl succinate (5) following a reported protocol [29]. Briefly, cholesteryl succinate (5) (3.4 g, 6.7 mmol) and epoxide 3 (1.26 g, 5.89 mmol) were added to [bmim]Br (3.1 g, 14.2 mmol).…”

“…The synthesis started with the preparation of key intermediates 3 and 5. The reaction of 3 with 5 followed a green ionic liquid-catalyzed epoxide ring opening methodology [29], which furnished 6 in excellent yield. Allylation of 6 led to monomer 7, which was readily copolymerized with MAA, using DVB as a crosslinker and AIBN as an initiator, in scCO 2 .…”

Ionic Liquid Functionalized Metal–Organic Framework ([DEIm][PF6]@MOF-5): Synthesis, Characterization, and Catalytic Application in the Reduction of 4-Nitrophenol

“…Because of a characteristic five-membered imidazole ring, imidazolium ionic liquids (ILs) have recently become superior functional materials. This is because of their nonflammability, low volatility, high thermal stability, and other characteristics. − They have been employed in organic reactions such as epoxide ring-opening reaction, biodiesel synthesis, to enhance oil recovery, and 4-NP reduction . Imidazolium ILs containing a hexafluorophosphate anion [PF 6 – ] have gained attention because of their thermophysical properties, the solubility of gases on them, and some other applications .…”