Reaktion #936207

Reaktionsgleichung

hydrochloric acid

Phenylpropylmagnesium bromide

Diethylchlorophosphite

water

→

3-phenylpropylphosphinic acid

Ausbeute 53.2%

Lösungsmittel

diethyl ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeA thick white slurry formed
2. 2
   FiltrationThe mixture was filtered under a nitrogen atmosphere
3. 3
   Sonstigethe filtrate evaporated under reduced pressure
4. 4
   Sonstigeto give a clear and colorless liquid
5. 5
   SonstigeAn exothermic reaction
6. 6
   workup.STIRRINGstirring
7. 7
   workup.WAITcontinued for 20 minutes
8. 8
   Extraktionfollowed by extraction with ethyl acetate
9. 9
   Waschenwashed with brine
10. 10
    Trocknendried (MgSO4)
11. 11
    Sonstigeevaporated
12. 12
    workup.ADDITIONTo the clear liquid was added sodium hydroxide (40 mL, 2.0 M NaOH)
13. 13
    workup.STIRRINGthe resulting solution stirred for 1 hour
14. 14
    Waschenwashed with diethyl ether
15. 15
    Extraktionextracted twice with ethyl acetate
16. 16
    Trocknendried (MgSO4)
17. 17
    Sonstigeevaporated

Vorschrift

Diethylchlorophosphite (15.7 g, 0.1 mol) in 50 mL of dry diethyl ether was cooled to 5° C. under an atmosphere of nitrogen. Phenylpropylmagnesium bromide (100 mL, 0.1 mol, 1.0 M solution of in Et2O) was added dropwise over 2 hours while maintaining a temperature between 0-10° C. A thick white slurry formed and was stirred an additional 30 minutes. The mixture was filtered under a nitrogen atmosphere and the filtrate evaporated under reduced pressure to give a clear and colorless liquid. To the liquid was added 20 mL of water followed by 0.5 ml of concentrated hydrochloric acid. An exothermic reaction was observed and stirring continued for 20 minutes followed by extraction with ethyl acetate. The organics were combined, washed with brine, dried (MgSO4) and evaporated. To the clear liquid was added sodium hydroxide (40 mL, 2.0 M NaOH), the resulting solution stirred for 1 hour and then washed with diethyl ether. The aqueous layer was acidified to pH 1.0 with concentrated hydrochloric acid and extracted twice with ethyl acetate. The organics were combined, dried (MgSO4) and evaporated to give 3-phenylpropylphosphinic acid (1, R=CH2CH2CH2Ph, R1=H) (9.8 g, 53%) as a clear and colorless oil.

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