Polymer supported nitrite esters as diazotising reagent

Summary

Glycidyl methacrylate based terpolymer resin was prepared in spherical beads form by suspension polymerization of glycidyl methacrylate (0.4mol)-methyl methylacrylate (0.5mol)-divinyl benzene (0.1mol) mixture. Acid catalysed reaction of the resin beads (110–220 μm ) with excess of glycerol gives corresponding modified resin with hydroxyl functions ( 6.86 mmol g⁻¹). Upon standing in 2 M HNO₂ solution, hydroxyl groups of the later esterified with nitrous acid (3.55 mmol g⁻¹). The nitrite ester functions of the resin have been demonstrated to be efficient nitrous acid precurser in diazotisation of aromatic amines. Diazotisation of aniline in 2 M HCl solutions at 0°C takes place in less than 15 minutes. Applicability and pratical yields of the method presented have been investigated by diazo coupling reaction of β- naphthol.