Formaldehyde → Diethyl phosphonomethanol

HRID 1646095Notes

Reaction equation

HRID 1646095 reaction equation
[P:1]([O-:8])([O:5][CH2:6][CH3:7])[O:2][CH2:3][CH3:4].[CH2:9]=[O:10].C(N(CC)CC)C>>[OH:10][CH2:9][P:1](=[O:8])([O:5][CH2:6][CH3:7])[O:2][CH2:3][CH3:4]

Participants

4

Reactant 3

HCID 712FormaldehydeHCID 8471TriethylamineHCID 3780918Diethylphosphite

Product 1

HCID 76513Diethyl phosphonomethanolYield 68.4%

Procedure

The procedure of Kluge was followed (Org. Syn. 1986, Vol. 64, 80-84). The following ingredients were combined: 69 g (0.50 mol) of diethyl phosphite, 15 g (0.50 mol) of paraformaldehyde, and 5.1 g (0.05 mol) of triethylamine. The stirred mixture was immersed in a preheated oil bath at 120° C. and heated for one hour. Upon cooling, the triethylamine was removed on the rotary evaporator at 80° C., and the residue was then distilled bulb-to-bulb (150-160° C., 0.10 mm) to provide 57.5 g (68%) of title compound as a colorless liquid.

Workup

  1. customThe stirred mixture was immersed in a preheated oil bath at 120° C.
  2. temperatureheated for one hour
  3. temperatureUpon cooling
  4. customthe triethylamine was removed on the rotary evaporator at 80° C.
  5. distillationthe residue was then distilled bulb-to-bulb (150-160° C., 0.10 mm)

Sources & evidence

ORD record
ord-b9b7794d504c402fb98ed6769ce0dd52
Source dataset
uspto-grants-1993_01
Patent number
US05177239

Reaction notes

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