Formaldehyde → Phosphonic acid, P,P'-ethenylidenebis-, P,P,P',P'-tetrakis(1-methylethyl) ester

HRID 2165340Notes

Reaction equation

HRID 2165340 reaction equation
[CH2:1]([P:12](=[O:21])([O:17][CH:18]([CH3:20])[CH3:19])[O:13][CH:14]([CH3:16])[CH3:15])[P:2](=[O:11])([O:7][CH:8]([CH3:10])[CH3:9])[O:3][CH:4]([CH3:6])[CH3:5].C=O.[CH2:24](NCC)C>CO>[C:1]([P:2](=[O:11])([O:7][CH:8]([CH3:9])[CH3:10])[O:3][CH:4]([CH3:6])[CH3:5])([P:12](=[O:21])([O:13][CH:14]([CH3:16])[CH3:15])[O:17][CH:18]([CH3:20])[CH3:19])=[CH2:24]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 8021DiethylamineHCID 74266Tetraisopropyl methylenediphosphonate

Product 1

HCID 4488726Phosphonic acid, P,P'-ethenylidenebis-, P,P,P',P'-tetrakis(1-methylethyl) esterYield 24.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

11.95 g (34.7 mmol) of tetraisopropyl methylenebisphosphonate, 5.2 g (173.5 mmol) of paraformaldehyde and 2.54 g (34.7 mmol) of diethylamine are combined with the same reactants and at the same conditions as described above in Example I. This mixture is then refluxed for 117 hours. After the methanol has been eliminated as described above in Example I, 3.0 g of tetraisopropyl ethenylidenebisphosphonate is produced as a clear liquid.

Workup

  1. temperatureThis mixture is then refluxed for 117 hours

Sources & evidence

ORD record
ord-58ee828ed9df4532ab6df08341382de5
Source dataset
uspto-grants-1990_07
Patent number
US04939284

Reaction notes

Loading…