Formaldehyde → Diethyl P-[[[(4-methylphenyl)sulfonyl]oxy]methyl]phosphonate

HRID 1890235Notes

Reaction equation

HRID 1890235 reaction equation
[P:1]([O-:8])([O:5][CH2:6][CH3:7])[O:2][CH2:3][CH3:4].C=O.P([O-])(OCC)([O:13][CH2:14]C)=O.C1(C)C=CC=CC=1.[C:27]1([CH3:37])[CH:32]=[CH:31][C:30]([S:33](Cl)(=[O:35])=[O:34])=[CH:29][CH:28]=1>C(N(CC)CC)C.C1(C)C=CC=CC=1>[C:27]1([CH3:37])[CH:32]=[CH:31][C:30]([S:33]([O:13][CH2:14][P:1](=[O:8])([O:5][CH2:6][CH3:7])[O:2][CH2:3][CH3:4])(=[O:35])=[O:34])=[CH:29][CH:28]=1

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 3780918DiethylphosphiteHCID 5166299Diethyl phosphoric acidHCID 19372395HCID 19372395, compound

Product 1

HCID 4193599Diethyl P-[[[(4-methylphenyl)sulfonyl]oxy]methyl]phosphonate

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8471TriethylamineSolvent2×

Procedure

To a reaction vessel containing inert atmosphere, e.g., nitrogen, was added diethyl phosphite, paraformaldehyde, triethylamine and toluene, the mixture was heated for 4-8 hours until TLC showing no diethyl phosphate remaining. After cooling to below 0° C., to the mixture was added a solution of p-toluenesulfonyl chloride toluene and triethylamine, after completion of the reaction, diethyl p-toluenesulfonyloxymethylphosphonate (C) was obtained;

Workup

  1. additionTo a reaction vessel containing inert atmosphere, e.g., nitrogen
  2. temperaturethe mixture was heated for 4-8 hours until TLC
  3. temperatureAfter cooling to below 0° C., to the mixture
  4. customafter completion of the reaction

Sources & evidence

ORD record
ord-96728319fec44c9082ed56570e306a5b
Source dataset
uspto-grants-2013_08
Patent number
US08507463B2

Reaction notes

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