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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1461868Generated: November 1, 2026

Formaldehyde → Dimethyl {[benzyl(hydroxy)amino]methyl}phosphonate

https://huagongshe.com/reaction/1461868

Reaction equation

Participants

RoleNameHCIDCharge
ReactantFormaldehydeHCID 712—
ReactantSodium BicarbonateHCID 516892—
ReactantN-benzylhydroxylamine hydrochlorideHCID 11332622—
ReactantDimethylphosphiteHCID 21884954—
SolventTetrahydrofuranHCID 8028—
ProductDimethyl {[benzyl(hydroxy)amino]methyl}phosphonateHCID 1988377782.9%

Reaction Conditions

Temperature55 °C

Reaction Steps

Using the procedure of Example 1, the above-named compound is prepared from 5.0 g (31 mmol) of N-benzylhydroxylamine hydrochloride, 1.8 g (60 mmol) of paraformaldehyde, 3.7 ml (40 mmol) of dimethyl phosphite, 2.5 g (30 mmol) of sodium bicarbonate and 350 ml of THF by heating at 55° C. for seven hours. The residue is purified by column chromatography (silica gel, methylene chloride: ethyl acetate eluent) to give 6.1 g (80% yield) of a viscous colorless liquid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS05077329
Source datasetuspto-grants-1991_12
ORD IDord-2eece80b6fa847549995c310abe10255
Source noteuspto-grants-1991_12