Triethylamine → 4-Phenylbutylphosphonous acid

Temperature

77 °C

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%.

1. distillationAcetonitrile was distilled off at 40° C. under vacuum
2. additionthe reaction mixture was diluted with water (20 ml)
3. extractionThe aqueous medium was extracted with dichloromethane (20 ml)
4. dry with materialdried over anhydrous sodium sulfate
5. distillationthe solvent distilled off

ORD record

ord-121f9985335d4a2a8314861421eb0cb5

Source dataset

uspto-grants-2004_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06717007B1