Formaldehyde → Tetramethyl ethenylidenebisphosphonate

HRID 620136Notes

Reaction equation

HRID 620136 reaction equation
[CH2:1]([P:8](=[O:13])([O:11][CH3:12])[O:9][CH3:10])[P:2](=[O:7])([O:5][CH3:6])[O:3][CH3:4].C=O.[CH2:16](NCC)C>CO>[C:1]([P:2](=[O:7])([O:5][CH3:6])[O:3][CH3:4])([P:8](=[O:13])([O:9][CH3:10])[O:11][CH3:12])=[CH2:16]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 8021DiethylamineHCID 519206Tetramethyl methylenediphosphonate

Product 1

HCID 13661367Tetramethyl ethenylidenebisphosphonateYield 71.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Tetramethyl ethenylidenebisphosphonate was synthesized via following general synthetic procedure. ##STR12## Specifically, 4.03 g (17.4 mmol) of tetramethyl methylenebisphosphonate, 2.60 g (86.7 mmol) of paraformaldehyde and 1.27 g (17.4 mmol) diethylamine were combined with the same reactants and at the same conditions as described above in Example 1 and refluxed for 2 hours. After the methanol was eliminated as described in Example I, 3.05 g of tetramethyl ethenylidenebisphosphonate was produced as a clear liquid with the following spectral characteristics: 1H NMR (CDCl3) 6.99 (distorted dd, 2H H2C=, J=33.9 and 37.7), (distorted dd, 12H, --OCH3, J=5.1 and 6.1); 13C NMR (CDCl3) 150.2 (s, H2C=), 130.2 (t, PCP, J=168), 53.2 (s, --OCH3); 31P NMR (CDCl3) +15.5.

Workup

  1. customTetramethyl ethenylidenebisphosphonate was synthesized
  2. temperaturerefluxed for 2 hours

Sources & evidence

ORD record
ord-3969d7ca8d284309897db4a30ce534b7
Source dataset
uspto-grants-1989_04
Patent number
US04820698

Reaction notes

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