PhCOCl-Py/Basic Alumina as a Versatile Reagent for Benzoylation in Solvent-Free Conditions

Satya Paul,Puja Nanda,Rajive Gupta

doi:10.3390/80400374

Abstract

A solvent-free procedure using PhCOCl-Py/basic alumina under microwave irradiation has been developed for N-, O- and S-benzoylation.

Highlights

Benzoylation is an important transformation in Organic Synthesis [1]
We report a simple procedure for the benzoylation of amino, hydroxy and thiol groups under solvent-free conditions using PhCOCl-Py/basic alumina
Benzoylation of aniline using benzoyl chloride over different solid supports in presence of various catalysts was studied in order to select the most efficient combination (Table 1)

Summary

Introduction

Benzoylation is an important transformation in Organic Synthesis [1]. A number of reagents can be used for carrying out this reaction, such as benzoyl chloride [1], benzoic anhydride [2], benzoyltetrazole [3], 2-benzoyl-1-methylpyridinium chloride [4], S-benzoic-O,O-diethylphosphorodithoic anhydride [5], benzoyl cyanide [6], etc. The reaction is usually catalyzed by bases like pyridine, triethylamine and sodium hydroxide[7]. Organic reactions on solid supports [8], and those assisted by microwaves, especially under solvent-free conditions [9], have attracted much attention because of their enhanced selectivity, milder reaction conditions and associated ease of manipulation. Acetyl chloride did not work under these conditions, development of a solvent-free protocol, meeting Green Chemistry principles is desirable

Results and Discussion

Boiling point

Conclusions

General Synthetic Procedure

Spectral and Analytical Data of Selected Compounds