Triethylamine → Butyl(ethoxy)phosphinic acid

HRID 483997Notes

Reaction equation

HRID 483997 reaction equation
[CH2:1]([PH:5](=[O:7])[OH:6])[CH2:2][CH2:3][CH3:4].C(N(CC)CC)C.[CH2:15]([O:17]C(Cl)=O)[CH3:16]>ClCCl>[CH2:15]([O:17][P:5]([CH2:1][CH2:2][CH2:3][CH3:4])(=[O:6])[OH:7])[CH3:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 178454911HCID 178454911, compound

Product 1

HCID 5272049Butyl(ethoxy)phosphinic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

51 g of n-butylphosphinic acid are dissolved in 200 ml of dichloromethane, the solution is cooled to 10°, and 42.3 g of triethylamine are added dropwise. An exothermic reaction takes place. The mixture is cooled to 10° again and 45.3 g of chloroformic acid ethyl ester are added dropwise within a period of 75 minutes. A precipitate forms in an exothermic reaction with the evolution of gas. A further 200 ml of dichloromethane are then added and the mixture is allowed to warm to room temperature and is then stirred for 2 hours at room temperature, washed with water and dried over sodium sulfate, and the organic solvent is removed. The crude product is distilled under a high vacuum, yielding n-butyl-phosphonic acid ethyl ester having a boiling point of 95° (5×10-5 bar).

Workup

  1. temperaturethe solution is cooled to 10°
  2. customAn exothermic reaction
  3. temperatureThe mixture is cooled to 10° again
  4. customA precipitate forms in an exothermic reaction with the evolution of gas
  5. washwashed with water
  6. dry with materialdried over sodium sulfate
  7. customthe organic solvent is removed
  8. distillationThe crude product is distilled under a high vacuum

Sources & evidence

ORD record
ord-c24451043fbc42b182b6f205c5af9c59
Source dataset
uspto-grants-1993_07
Patent number
US05229379

Reaction notes

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