Hydrogen Peroxide → HCID 22902905, compound

Participants

Reaction Steps

A solution of 688 parts of methylacrylate in 285 parts of toluene is reacted with 450 parts of 80% isobutylphosphine in the presence of 3.9 parts of (azobisisobutyronitrile) initiator at 74°-93° C. for 7 hours. The resulting isobutylbis(carbomethoxyethyl)phosphine is oxidized with 600 parts of (10% excess) of 25% aqueous hydrogen peroxide. The reaction is complete within 2-3 hours at 65° C. and the resultant phosphine oxide is isolated as an oil following distillation of toluene and water from the mixture. The recovered phosphine oxide is hydrolyzed in 4 liters of 5% aqueous sulfuric acid solution by refluxing over a 7 hour period. On cooling, the product, isobutyl bis(β-carboxyethyl)phosphine oxide is isolated as a white crystalline solid in 70% yield and purified by recrystallization from water, m.p. 186°-187° C.

Provenance & Evidence