Phenol → NMPD Phenol

Phenol (18.87 g, 0.20 mol), 2-nitro-2-methyl-1,3-propanediol (27.02 g, 0.20 mol) and sodium phenylate trihydrate (0.25 g, 1.5 mmol) were charged into a 3-neck flask equipped with a mechanical stirrer, distillation head with graduated receiver, thermocouple for temperature control, and nitrogen blanket/vacuum port. Under N2, stirring and heating were initiated, brining the internal reaction temperature up to 140 C. After about 10 minutes, a slow distillation of an imniscible mixture of oil/water began. The reaction was held at 140 C for 3 hours during which time a total of 11 mL of distillate was collected (7.8 mL aqueous, 3.2 mL organic oil). Vacuum (80 torr) was then applied to the reaction mass to remove the final traces of oil/water. After 15 minutes under vacuum, an additional 1.9 mL of distillate was collected (1 mL aqueous, 0.9 mL oil) and the distillation had essentially stopped. The reaction was terminated by cooling to room temperature. A dark, glassy solid weighing approximately 29 g was collected. An aliquot of this product (10.0 g) was dissolved in 20 g 1,3-dioxolane solvent. Once complete dissolution was obtained, Sigmacure 7720 Part I Phenolic Resin (60.5 g, HA International) was slowly added with vigorous stirring. The resulting product was a very dark solution free from suspended solids.