Formaldehyde → Dibenzyl (hydroxymethyl)phosphonate

HRID 617892Notes

Reaction equation

HRID 617892 reaction equation
[P:1]([O-:18])([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[O:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH2:19]=[O:20]>C(N(CC)CC)C>[OH:20][CH2:19][P:1](=[O:18])([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[O:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 21904359Dibenzylphosphite

Product 1

HCID 14079960Dibenzyl (hydroxymethyl)phosphonate

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
55 °C

Procedure

100 ml of dibenzyl phosphite, 12.5 g of paraformaldehyde and 6.2 ml of triethylamine were mixed together with stirring. On slow warming to 55° C., a temperature increase to 120° C. took place. The solution, which was now clear, was allowed to cool to 90° C. and was stirred at this temperature for a further 30 minutes. After cooling to room temperature, it was chromatographed on 1 kg of silica gel at elevated pressure (eluent: n-hexane/ethyl acetate 1:4). After concentrating the fractions and drying the residue in vacuo at 60° C. for 12 hours, 96.1 g of pure, oily dibenzyl hydroxymethylphosphonate were obtained, which was reacted without further purification.

Workup

  1. temperaturea temperature increase to 120° C.
  2. temperatureto cool to 90° C.
  3. stirringwas stirred at this temperature for a further 30 minutes
  4. temperatureAfter cooling to room temperature
  5. customit was chromatographed on 1 kg of silica gel at elevated pressure (eluent: n-hexane/ethyl acetate 1:4)
  6. concentrationAfter concentrating the fractions
  7. customdrying the residue in vacuo at 60° C. for 12 hours

Sources & evidence

ORD record
ord-8111d19d4cac46298e1ecfc7756e2fcd
Source dataset
uspto-grants-1999_09
Patent number
US05952327

Reaction notes

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