Triethylamine → 4-Phenylbutylphosphonous acid

Participants

Reaction Conditions

Reaction Steps

To a 30 wt % aqueous solution of hypophosphorous acid (41.8 ml, 0.19 moles) in acetonitrile (100 ml) was added 4-phenyl-1-butene (5 gm, 0.038 moles) and sodium persulfate (1.8 gm, 0.00756 moles). To the stirred mixture triethylamine was added and the pH of the reaction mixture was adjusted to 6.5±0.5. The reaction mixture was heated at 77° C. for 15 minutes for the reaction to be complete. Acetonitrile was distilled off at 40° C. under vacuum and the reaction mixture was diluted with water (20 ml). The pH of the mixture was adjusted to 8.5 with 50% aqueous sodium hydroxide followed by acidification to a pH of 5.0±0.2. The aqueous medium was extracted with dichloromethane (20 ml) and kept aside. The pH of the aqueous layer was adjusted to 1-1.5 using conc. H2SO4 and reextracted with dichloromethane (2×20 ml). The total organic layers were combined, dried over anhydrous sodium sulfate and the solvent distilled off to yield 6.6 gm (88.0%) of the title compound as an oil, having a purity 97.6%.

Provenance & Evidence