Acyloin condensation of terephthaloyl chloride—a novel route to polyhydroxyketones

Acyloin condensation of terephthaloyl chloride under homogeneous conditions using a sodium naphthalene radical anion system and under heterogeneous conditions using finely dispersed molten sodium with varying ratios of sodium to organic substrate gave mainly polymeric materials that were identified as polyhydroxyketones. IR, NMR, and DTA analyses indicate that these polymers are copolymers of benzoin and benzil hitherto unknown. The yields of polymers under homogeneous conditions were higher than those obtained under heterogeneous conditions, but the molecular weight distribution was similar to those obtained with molten sodium.