Pyridine → 2-(4-t-Butylazo-4-cyanovaleryloxy)-2'-hydroxybenzophenone

Participants

Reaction Steps

To a solution of 4.68 g. (0.0218 m) of 2,2'-dihydroxybenzophenone and 2.5 ml. of pyridine in 30 ml. of ether in a 4 neck 100 ml. round bottom flask equipped with a thermometer, condenser and magnetic stirring bar was added 5.0 g. (0.0218 m) of 4-t-butylazo-4-cyanovaleryl chloride dropwise with cooling so the temperature did not rise above 25° C. After completion of the addition the reaction mixture was stirred 1/2 hour at room temperature and then diluted with 100 ml. of water. The ether layer was separated, washed consecutively with 5% HCl, water, 10% NaHCO3 solution and saturated sodium chloride solution. The ether was evaporated off leaving a yellow solid. The solid was slurried in pentane, filtered and air dried. The product weighed 6.3 g. (71.2% yield) and decomposed slowly on heating above 80° C. The infrared spectrum of the product was in agreement with the structure of the desired product.

Provenance & Evidence