Reaction #9613

Reaction equation

hydrogen peroxide

sodium hypophosphite hydrate

1-hexene

hydrogen peroxide

→

n-hexylphosphinic acid

Yield 82.4%

Solvents

ethanol

sulfuric acid

Conditions

Workup

1. 1
   workup.ADDITIONwas added
2. 2
   TemperatureThe resulting mixture was refluxed for 8 hs
3. 3
   Temperatureto reflux for another 8 hs
4. 4
   TemperatureThe resulting mixture was cooled
5. 5
   Filtrationfiltered
6. 6
   Otherthe ethanol was removed
7. 7
   Othera rotary evaporator
8. 8
   workup.ADDITIONTo the resulting residue, 200 mL water was added
9. 9
   workup.ADDITION50% sodium hydroxide solution was added until the solution
10. 10
    ExtractionThe mixture was extracted twice with 200 mL diethyl ether
11. 11
    ExtractionThe aqueous layer was extracted with 200 mL ethyl acetate
12. 12
    Washthe organic layer was washed with saturated sodium chloride
13. 13
    Dryingdried over anhydrous magnesium sulfate
14. 14
    OtherThe organic layer was decanted
15. 15
    Washthe drying agent was washed with another 50 mL ethyl acetate
16. 16
    OtherThe combined organic layers were evaporated on a rotary evaporator

Procedure

To a mixture of 95.2 g (0.898 mol) of sodium hypophosphite hydrate in 600 mL 95% ethanol, 23.8 mL of concentrated sulfuric acid was added. 1-hexene (25.2 g, 0.30 mol) was added to the stirred mixture followed by 1.76 g (0.0155 mol) of 30% hydrogen peroxide. The resulting mixture was refluxed for 8 hs, and then another 1.14 g (0.0101 mol) of hydrogen peroxide was added and the reaction mixture was continued to reflux for another 8 hs. The resulting mixture was cooled, filtered, and then the ethanol was removed using a rotary evaporator. To the resulting residue, 200 mL water was added and then 50% sodium hydroxide solution was added until the solution became alkaline. The mixture was extracted twice with 200 mL diethyl ether, and the aqueous phase was then acidified with concentrated sulfuric acid. The aqueous layer was extracted with 200 mL ethyl acetate, and the organic layer was washed with saturated sodium chloride and then dried over anhydrous magnesium sulfate. The organic layer was decanted and the drying agent was washed with another 50 mL ethyl acetate. The combined organic layers were evaporated on a rotary evaporator. 37.0 g n-hexylphosphinic acid (82.4% yield) was obtained.

Source