Abstract
Aqueous tetra-n-butyl ammonium hydroxide solution (TBAOH) is an efficient catalyst for the acylation of alcohols, phenols and thiols. This procedure is convenient, simple and suitable for the synthesis of esters and thioesters in high yields.
Highlights
One of the most important priorities within organic chemistry research is to find methods and processes more compatible and more economical compared to preceding methods
Some of the above described methods require the use of harshreaction conditions, hazardous materials, excess acylating agent, long reaction time, high temperature and low yields.still it is of great importance to find new useful and environmentally friendly methods with use of base catalysts for the acylation of alcohols, phenols and thiols
In order to optimize of the reaction conditions in terms of the amount of tetra-n-butyl ammonium hydroxide solution (TBAOH) (20% in water), time and temperature, the reaction of benzyl alcohol (1.5 mmol) with acetic anhydride (1.0 mmol) and benzyl mercaptan (1.0 mmol) with acetic anhydride (1.2 mmol) were studied without the presence of solvent (Scheme 1) as models reactions
Summary
One of the most important priorities within organic chemistry research is to find methods and processes more compatible and more economical compared to preceding methods. In continuation of our interest in exploring new application of tetran-butyl ammonium hydroxide in organic synthetic methodologies [27,28,29,30,31,32,33,34] and attempts to develop previous methods, we wish to report acylation of alcohols, phenols under neat conditions in the presence of an aqueous solution of TBAOH at mild conditions. A diverserange of dialkyl (symmetric and unsymmetric) and aryl alkyl esters and thioesters was synthesized in good to excellent yields (80-92%) in the presence of 2 mL of aqueous solution of TBAOH (Scheme 2) in optimal reaction condition.
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