反応 #936207

反応方程式

hydrochloric acid

Phenylpropylmagnesium bromide

Diethylchlorophosphite

water

→

3-phenylpropylphosphinic acid

収率 53.2%

溶媒

diethyl ether

反応条件

後処理

1. 1
   その他A thick white slurry formed
2. 2
   ろ過The mixture was filtered under a nitrogen atmosphere
3. 3
   その他the filtrate evaporated under reduced pressure
4. 4
   その他to give a clear and colorless liquid
5. 5
   その他An exothermic reaction
6. 6
   workup.STIRRINGstirring
7. 7
   workup.WAITcontinued for 20 minutes
8. 8
   抽出followed by extraction with ethyl acetate
9. 9
   洗浄washed with brine
10. 10
    乾燥dried (MgSO4)
11. 11
    その他evaporated
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
    洗浄washed with diethyl ether
15. 15
    抽出extracted twice with ethyl acetate
16. 16
    乾燥dried (MgSO4)
17. 17
    その他evaporated

実験手順

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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