Tetrabutylammonium tribromide mediated condensation of carboxylic acids with alcohol

Abstract

The direct condensation of various carboxylic acids and alcohols was achieved efficiently at reflux temperature under a solvent free condition using a catalytic amount of tetrabutylammonium tribromide (TBATB). Chemoselective acylation of primary alcohols in presence of secondary alcohols and phenols has been achieved. Steric factors in carboxylic acids played a crucial role during chemoselective acylation of diols. Reaction under a solvent free condition, absence of any dehydrating agent or use of any special techniques for removal of water and higher yields are the important features of this protocol.

Synthetic utility of biomimicking vanadium bromoperoxidase and n-tetrabutylammonium tribromide (TBATB) in organic synthesis

“…TBATB has been used for several important functional group transformations. 106–109 In 2006, Patel et al transformed various alcohols into esters through acylation using carboxylic acids (Scheme 30A). 106 The reaction was chemoselective in nature, where primary alcohols were chemoselectively acylated in the presence of secondary alcohols and phenols.…”

“…106–109 In 2006, Patel et al transformed various alcohols into esters through acylation using carboxylic acids (Scheme 30A). 106 The reaction was chemoselective in nature, where primary alcohols were chemoselectively acylated in the presence of secondary alcohols and phenols. The transformation of alcohols into esters was achieved in high yields under mild reaction conditions.…”

Highly Efficient One‐pot Aerobic Synthesis of α‐Aminophosphonate from Alcohols: Dual Catalytic Effect of Tetrabutylammonium Tribromide (TBATB)

“…[22][23][24][25][26][27] Orange crystalline solid TBATB is known as a mild and efficient agent for bromination of alkenes, alkynes, synthesis of α-bromo acetals, condensation of carbonyl compounds, regioselective bromination of aromatic amines, selective bromina-tion of phenols, preparation of α-bromo enones, determination of unsaturation number, catalytic protection-deprotection of carbonyl compounds, oxidizing bromination, and oxidation of benzyl alcohols, aliphatic aldehydes, sulfoxides, and amino acids. [28][29][30][31][32][33][34] Very recently, we presented TBATB as an agent for alcohol and toluene oxidation under visible blue light irradiation (465 nm) under mild and green conditions. [18,35] According to our knowledge, to date, there are two reports on the synthesis of one-pot α-aminophosphonates from benzyl alcohols: (a) the first work was done in 2017 by Kaboudin et al In this work, first imines were prepared through aerobic oxidation of alcohol in the presence of NaOH for 4 days at toluene using CuO@Fe 3 O 4 magnetic nanoparticles.…”

“…Reaction condition: First step-10 mg TBATB, Air atmosphere, 8 ml CH 3 CN, 3 h oxidation, LED (4*3 W) and second step 5 h reflux condition. [b] Reported based on31 P NMR [c] In the absence of TBATB ChemistrySelect Two steps one-pot synthesis of α-aminophosphonate via tunable aerobic photocatalytic oxidation of alcohols to aldehydes, and reaction with anilines and diethylphosphite (or diisopropylphosphite) using TBATB.…”

Synthesis, Characterization and Optimization of Oleyl Oleate Wax Ester Using Ionic Liquid Catalysts

“…However, the supply of jojoba oil is inconsistent and sperm whale oil is diminishing, so a substitute for this wax ester is desired [3]. Esterification of carboxylic acids with alcohols using homogeneous and heterogeneous catalysts is well documented in the literature [4][5][6]. However, several limitations, such as an excess of the catalysts or amounts of reactants to achieve efficient conversion, removal of water during the reaction, long reaction times, and large amounts of effluent generation during work-up are associated with these processes [7].…”