Formaldehyde → Diisopropyl hydroxymethylphosphonate

HRID 617900Notes

Reaction equation

HRID 617900 reaction equation
[P:1]([O-:10])([O:6][CH:7]([CH3:9])[CH3:8])[O:2][CH:3]([CH3:5])[CH3:4].[CH2:11]=[O:12]>C(N(CC)CC)C>[OH:12][CH2:11][P:1](=[O:10])([O:6][CH:7]([CH3:9])[CH3:8])[O:2][CH:3]([CH3:5])[CH3:4]

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 21884976Phosphorous acid, bis(1-methylethyl) ester

Product 1

HCID 10867235Diisopropyl hydroxymethylphosphonateYield 67.5%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

50.0 g of diisopropyl phosphite, 8.5 g of paraformaldehyde and 4.0 ml of triethylamine were reacted according to the method indicated in Example 1A). Chromatography of the crude product on silica gel (eluent: n-hexane/ethyl acetate 1:4) yielded 37.5 g of diisopropyl hydroxymethylphosphonate as an oil, which was reacted further without purification.

Sources & evidence

ORD record
ord-2f4441f1744f41ee88c6ae8dc67b45b4
Source dataset
uspto-grants-1999_09
Patent number
US05952327

Reaction notes

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