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General procedure: Phenol (0.5 mmol), benzyl bromide(1.2 mmol) and KOH (2.0 mmol) was added to the DES (1 mL) and heated at temperature (80°C) for 2 h. After cooling to room temperature water was added and the product was extracted with ethyl acetate (1 3 mL) andanalyzed by GC–MS after the addition of hexamethylbenzene as an internal standard. The product was purified using column chromatography on silica gel(hexane/EtOAc::99:1). The pure product was characterized by 1H NMR and 13CNMR.Table 4 Comparison of different methodologies for benzylation of phenols with benzyl bromide
EXAMPLE 1 There are prepared 4-dibutylaminopyridine by adding 0.1 mole of 4-hydroxypyridine and 15 grams of phosphorous pentoxide in the presence of 0.2 mole of dibutylamine at 250° C. for 16 hours. The dimethylaminopyridine was obtained from the Aldrich Chemical Company of Milwaukee, Wis. and the 4-pyrrolidinopyridine was obtained from the Reilley Tar and Chemical Company, Indianapolis, Ind.
In dibutylamine;
Example 1. There was prepared 4-dibutylaminopyridine by adding 0.1 mole of 4-hydroxypyridine and 15 grams of phosphorous pentoxide in the presence of 0.2 mole of dibutylamine at 250oC for 16 hours. The dimethylaminopyridine was obtained from the Aldrich Chemical Company of Milwaukee, Wisconsin and the 4-pyrrolidinopyridine was obtained from the Reilley Tar and Chemical Company, Indianapolis, Indiana.
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