Lithium hydroxide, monohydrate → HCID 9856380, compound

HRID 2050707Notes

Reaction equation

HRID 2050707 reaction equation
O.[OH-].[Li+].[NH2:4][CH2:5][CH2:6][CH2:7][P:8]([CH:13]([O:18][CH2:19][CH2:20][CH3:21])[O:14][CH2:15][CH2:16][CH3:17])(=[O:12])[O:9]CC>O.C(O)C>[NH2:4][CH2:5][CH2:6][CH2:7][P:8]([CH:13]([O:18][CH2:19][CH2:20][CH3:21])[O:14][CH2:15][CH2:16][CH3:17])(=[O:9])[OH:12]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 19090926HCID 19090926, compound

Product 1

HCID 9856380HCID 9856380, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

To a stirred solution of 0.05 g of lithium hydroxide monohydrate in 7.7 ml of water, is added a solution of 4.37 g of ethyl 3-aminopropyl(di-n-propyloxymethyl)phosphinate in 16.2 ml of ethanol. A slight exothermic reaction ensues and the reaction mixture becomes cloudy. A further 2 ml of water are added and the clear solution stirred at room temperature for 5 days. After this time the mixture is concentrated in vacuo at 55° and the residue redissolved in water and extracted with 3×10 ml of dichloromethane. The aqueous layer is again evaporated to dryness and the residue dissolved in 20 ml of water and treated with 0.51 ml of 85% phosphoric acid. After stirring overnight, the solid is removed by filtration. Evaporation of the filtrate and crystallisation of the residue from ethanol/ether affords 3-aminopropyl(di-n-propyloxymethyl)phosphinic acid, m.p. 223-225°, as a white solid.

Workup

  1. customA slight exothermic reaction ensues
  2. concentrationAfter this time the mixture is concentrated in vacuo at 55°
  3. dissolutionthe residue redissolved in water
  4. extractionextracted with 3×10 ml of dichloromethane
  5. customThe aqueous layer is again evaporated to dryness
  6. dissolutionthe residue dissolved in 20 ml of water
  7. additiontreated with 0.51 ml of 85% phosphoric acid
  8. stirringAfter stirring overnight
  9. customthe solid is removed by filtration
  10. customEvaporation of the filtrate and crystallisation of the residue from ethanol/ether

Sources & evidence

ORD record
ord-5586b368944b402d85e8f0f80227aa6d
Source dataset
uspto-grants-1991_05
Patent number
US05013863

Reaction notes

Loading…