Hydrochloric Acid → HCID 178527054, compound

HRID 849025Notes

Reaction equation

HRID 849025 reaction equation
C([O:3][P:4](Cl)[O:5]CC)C.[C:9]1([CH2:15][CH2:16][CH2:17][Mg]Br)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.O.Cl>C(OCC)C>[C:9]1([CH2:15][CH2:16][CH2:17][PH:4](=[O:3])[OH:5])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 68530Ethyl phosphorochloriditeHCID 178418471HCID 178418471, compound

Product 1

HCID 178527054HCID 178527054, compoundYield 53.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
5 °C

Procedure

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.

Workup

  1. customA thick white slurry formed
  2. filtrationThe mixture was filtered under a nitrogen atmosphere
  3. customthe filtrate evaporated under reduced pressure
  4. customto give a clear and colorless liquid
  5. customAn exothermic reaction
  6. stirringstirring
  7. waitcontinued for 20 minutes
  8. extractionfollowed by extraction with ethyl acetate
  9. washwashed with brine
  10. dry with materialdried (MgSO4)
  11. customevaporated
  12. additionTo the clear liquid was added sodium hydroxide (40 mL, 2.0 M NaOH)
  13. stirringthe resulting solution stirred for 1 hour
  14. washwashed with diethyl ether
  15. extractionextracted twice with ethyl acetate
  16. dry with materialdried (MgSO4)
  17. customevaporated

Sources & evidence

ORD record
ord-eadc256e3bac424e96c9a78d2261f91e
Source dataset
uspto-grants-2000_01
Patent number
US06011021

Reaction notes

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