反应详情

A solution of sodium hypophosphite hydrate (17.6 g, 200 mmol), 4-phenyl-1-butene (10 mL, 66.6 mmol), 2,2′-azobisisobutyronitrile (AlBN) (1 g), conc. sulfuric acid (1 mL) in 200 mL of absolute ethanol was heated to reflux for 17 hours. The reaction mixture was concentrated to an oil, suspended in 70 mL of water, made basic with 50% NaOH and washed with 2×70 mL ether. The aqueous layer was acidified with conc. sulfuric acid, extracted into ethyl acetate and concentrated. The residue was dissolved in ether and adamantaneamine (10 g, 66 mmol) was added. A white precipitate was filtered, partitioned between 10% HCl and ethyl acetate. The organic layer was concentrated to provide 4-phenylbutylphosphinic acid (7.2 g).

1. temperatureto reflux for 17 hours
2. concentrationThe reaction mixture was concentrated to an oil
3. washwashed with 2×70 mL ether
4. extractionextracted into ethyl acetate
5. concentrationconcentrated
6. dissolutionThe residue was dissolved in ether
7. filtrationA white precipitate was filtered
8. custompartitioned between 10% HCl and ethyl acetate
9. concentrationThe organic layer was concentrated