Hydrochloric Acid → HCID 178503023, compound

HRID 1600599Notes

Reaction equation

HRID 1600599 reaction equation
C([O:3][P:4](Cl)[O:5][CH2:6][CH3:7])C.C([Mg]Cl)[C:10]1[CH:15]=[CH:14]C=[CH:12][CH:11]=1.O.Cl.[CH2:20](OCC)C>>[CH3:20][PH:4](=[O:3])[O:5][CH2:6][C:7]1[CH:14]=[CH:15][CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 3283Diethyl EtherHCID 68530Ethyl phosphorochloriditeHCID 178418336HCID 178418336, compound

Product 1

HCID 178503023HCID 178503023, compoundYield 32%

Procedure

Diethylchlorophosphite (25 g, 0.16 mol) in 100 mL of dry diethyl ether was cooled to 0° C. under an atmosphere of nitrogen. Benzylmagnesium chloride (80 mL, 0.16 mol, 2.0 M solution in Et2O) was added dropwise over two hours while maintaining a temperature below 10° C. A thick white slurry formed and stirring was continued at room temperature for 1 hour. 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 concentrated hydrochloric acid. An exothermic reaction was observed and stirring was continued for an additional 30 minutes followed by extraction with ethyl acetate. The organics were combined, washed with brine, dried (MgSO4) and evaporated. The clear light golden liquid was added to sodium hydroxide (50 mL, 2.0 M NaOH), stirred for 1 hour and washed 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 benzylphosphinic acid (1, R=CH2Ph, R1 =H) (8 g, 32%) as a clear light golden oil.

Workup

  1. temperaturewhile maintaining a temperature below 10° C
  2. customA thick white slurry formed
  3. filtrationThe mixture was filtered under a nitrogen atmosphere
  4. customthe filtrate evaporated under reduced pressure
  5. customto give a clear and colorless liquid
  6. additionwas added
  7. customAn exothermic reaction
  8. stirringstirring
  9. waitwas continued for an additional 30 minutes
  10. extractionfollowed by extraction with ethyl acetate
  11. washwashed with brine
  12. dry with materialdried (MgSO4)
  13. customevaporated
  14. additionThe clear light golden liquid was added to sodium hydroxide (50 mL, 2.0 M NaOH)
  15. stirringstirred for 1 hour
  16. washwashed with diethyl ether
  17. extractionextracted with ethyl acetate
  18. dry with materialdried (MgSO4)
  19. customevaporated

Sources & evidence

ORD record
ord-0163c7d1545140f6852005b99708cd5c
Source dataset
uspto-grants-1999_11
Patent number
US05977090

Reaction notes

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