Formaldehyde → Diisopropyl hydroxymethylphosphonate

HRID 249118Notes

Reaction equation

HRID 249118 reaction equation
[P:1]([O-:10])([O:6][CH:7]([CH3:9])[CH3:8])[O:2][CH:3]([CH3:5])[CH3:4].C(N(CC)CC)C.[CH2:18]=[O:19]>>[OH:19][CH2:18][P:1](=[O:10])([O:6][CH:7]([CH3:9])[CH3:8])[O:2][CH:3]([CH3:5])[CH3:4]

Participants

4

Reactant 3

HCID 712Formaldehyde2×HCID 8471TriethylamineHCID 21884976Phosphorous acid, bis(1-methylethyl) ester

Product 1

HCID 10867235Diisopropyl hydroxymethylphosphonateYield 91%

Procedure

A mixture of 33.2 g (0.20 mol) of diisopropyl phosphite, 2.8 ml (0.02 mol) of triethylamine, and 6.0 g (0.20 mol) of paraformaldehyde, was immersed in a 100° C. oil bath and then heated between 100°-120° C. for 45 minutes under nitrogen. An exotherm occurred within 10 minutes and all of the paraformaldehyde dissolved rapidly. The triethylamine was removed at reduced pressure, and the residue was bulb-to-bulb distilled in four portions to provide a total of 35.17 g (91%) of title compound as a colorless oil. TLC Silica gel (5:95 CH3OH:CH2Cl2) Rf =0.17

Workup

  1. customwas immersed in a 100° C.
  2. temperatureheated between 100°-120° C. for 45 minutes under nitrogen
  3. customThe triethylamine was removed at reduced pressure
  4. distillationdistilled in four portions

Sources & evidence

ORD record
ord-8d30567cfb2f4168b8b9bc61005f7e43
Source dataset
uspto-grants-1993_05
Patent number
US05212164

Reaction notes

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