Formaldehyde → HCID 18981637, compound

HRID 327001Notes

Reaction equation

HRID 327001 reaction equation
[CH2:1]=[O:2].CO.[CH2:5]([PH:8](=[O:12])[CH2:9][CH2:10][CH3:11])[CH2:6][CH3:7]>C(N(CC)CC)C>[CH2:5]([P:8](=[O:12])([CH2:9][CH2:10][CH3:11])[CH2:1][OH:2])[CH2:6][CH3:7]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 887MethanolHCID 178460678HCID 178460678, compound

Product 1

HCID 18981637HCID 18981637, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
70 °C

Procedure

A 37% of formaldehyde solution, 16.2 g, was added in small portions over a five minute period to solution of 40 ml of methanol, 21.78 g of di-n-propyl phosphine oxide, (Example 16), and 1.5 ml of triethylamine. The reaction exothermed to 30° C. and was allowed to stir for ten minutes before it was warmed to 70° C. for three hours. The reaction was then allowed to cool to room temperature and stand overnight. The reaction was concentrated, the concentrate dissolved in 70 ml of THF, filtered and reconcentrated. The concentrate was diluted with 60 ml of 1,4-dioxane which was distilled off to yield 19.8 g of the desired phosphine oxide as an oil.

Workup

  1. customexothermed to 30° C.
  2. temperatureto cool to room temperature
  3. concentrationThe reaction was concentrated
  4. dissolutionthe concentrate dissolved in 70 ml of THF
  5. filtrationfiltered
  6. additionThe concentrate was diluted with 60 ml of 1,4-dioxane which
  7. distillationwas distilled off

Sources & evidence

ORD record
ord-3e729d5623604a02b618b7fb9bd43772
Source dataset
uspto-grants-1993_12
Patent number
US05272128

Reaction notes

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