Bromoacetic Acid → (Diethoxyphosphinyl)acetic acid

HRID 1660312Notes

Reaction equation

HRID 1660312 reaction equation
[P:1]([O-:8])([O:5][CH2:6][CH3:7])[O:2][CH2:3][CH3:4].[O-]CC.[Na+].Br[CH2:14][C:15]([OH:17])=[O:16]>C(O)C>[C:15]([CH2:14][P:1](=[O:8])([O:5][CH2:6][CH3:7])[O:2][CH2:3][CH3:4])([OH:17])=[O:16]

Participants

5

Reactant 3

HCID 6227Bromoacetic AcidHCID 2723922Sodium ethoxideHCID 3780918Diethylphosphite

Product 1

HCID 36704(Diethoxyphosphinyl)acetic acidYield 154.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4.0 ml (0.031 mole) of diethyl phosphite, 6.68 g (0.093 mole) of 94% sodium ethoxide, and 4.32 g (0.031 mole) of bromoacetic acid in 50 ml of absolute ethanol was heated under reflux for 1 h. Solvent was removed at reduced pressure, and the residual solid was triturated with ethyl acetate and 15 ml of conc hydrochloric acid with shaking and portionwise addition of water until all the solid was dissolved. The ethyl acetate layer was separated, dried (over MgSO4), and evaporated to give 9.4 g of residual liquid diethyl carboxymethylphosphonate; 1H NMR spectrum confirmed the structure of this compound which is disclosed by Martin and Griffin, J. Org. Chem., 30, 4034-4038 (1965).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1 h
  3. customSolvent was removed at reduced pressure
  4. customthe residual solid was triturated with ethyl acetate and 15 ml of conc hydrochloric acid
  5. additionportionwise addition of water until all the solid
  6. dissolutionwas dissolved
  7. customThe ethyl acetate layer was separated
  8. dry with materialdried (over MgSO4)
  9. customevaporated

Sources & evidence

ORD record
ord-299c3e45bd60462bb839e9f797029b26
Source dataset
uspto-grants-1981_12
Patent number
US04307232

Reaction notes

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