Reaktion #464357

Reaktionsgleichung

hydrochloric acid

Phenethylmagnesium chloride

Diethylchlorophosphite

water

→

phenethylphosphinic acid

Ausbeute 58.0%

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
   workup.ADDITIONwas added
6. 6
   SonstigeAn exothermic reaction
7. 7
   workup.STIRRINGstirring
8. 8
   workup.WAITcontinued for 15 minutes
9. 9
   Extraktionfollowed by extraction with ethyl acetate
10. 10
    Waschenwashed with brine
11. 11
    Trocknendried (MgSO4)
12. 12
    Sonstigeevaporated
13. 13
    workup.STIRRINGstirred for 1 hour
14. 14
    Waschenwashed once with diethyl ether
15. 15
    Extraktionextracted with ethyl acetate
16. 16
    Sonstigedried (MgSo4)
17. 17
    Sonstigeevaporated

Vorschrift

Diethylchlorophosphite (15.6 g,0.1 mol) in 100 mL of dry diethyl ether was cooled to 5° C. under an atmosphere of nitrogen. Phenethylmagnesium chloride (100 mL, 0.1 mol, 1.0 M in THF) was added dropwise over 2 hours while maintaining a temperature between 0-10° C. A thick white slurry formed and stirred at room temperature overnight. The mixture was filtered under a nitrogen atmosphere and the filtrate evaporated under reduced pressure to give a clear and colorless liquid. The liquid was stirred as 15 mL of water was added followed by 0.5 mL of concentrated hydrochloric acid. An exothermic reaction was observed and stirring continued for 15 minutes followed by extraction with ethyl acetate. The organics were combined, washed with brine, dried (MgSO4) and evaporated. The clear liquid was brought up in sodium hydroxide (40 mL, 2.0 M NaOH), stirred for 1 hour and washed once with diethyl ether. The aqueous layer was acidified to pH 1.0 with concentrated hydrochloric acid and extracted with ethyl acetate. The organics were combined, dried (MgSo4) and evaporated to give phenethylphosphinic acid (1,R=CH2CH2Ph, R1=H)(9.8 g, 58%) as a clear light yellow oil.

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