tert-Butyl hydroperoxide → Diethyl butyrylphosphonate

HRID 1720116Notes

Reaction equation

HRID 1720116 reaction equation
[OH:1][CH:2]([P:6](=[O:13])([O:10][CH2:11][CH3:12])[O:7][CH2:8][CH3:9])[CH2:3][CH2:4][CH3:5].C/C(/[O-])=C/C(C)=O.C(OO)(C)(C)C>ClC1C=CC=CC=1>[C:2]([P:6](=[O:13])([O:7][CH2:8][CH3:9])[O:10][CH2:11][CH3:12])(=[O:1])[CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 6410tert-Butyl hydroperoxideHCID 519425Diethyl 1-hydroxybutylphosphonateHCID 5460482Acetylacetonate

Product 1

HCID 15001419Diethyl butyrylphosphonate

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

To 16.2 g (77 mmol) of diethyl α-hydroxybutylphosphonate and 0.4 g (1.5 mmol) of vanadyl(IV) bis-acetylacetonate in 100 g of chlorobenzene there were added 30.4 g (0.24 mol) of 70 wt % strength aqueous tert-butylhydroperoxide and the mixture was stirred for 4 days. The solvent was removed in vacuo. Yield (in the residue ): 25%

Workup

  1. customThe solvent was removed in vacuo
  2. customYield (in the residue ): 25%

Sources & evidence

ORD record
ord-3e3f9087fff94e57b366f6e70e9581ba
Source dataset
uspto-grants-1996_04
Patent number
US05504236

Reaction notes

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