tert-Butyl hydroperoxide → 2,6-Dichlorobenzoyl diphenylphosphine oxide

HRID 1489923Notes

Reaction equation

HRID 1489923 reaction equation
[OH:1][CH:2]([P:11](=[O:24])([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:3]1[C:8]([Cl:9])=[CH:7][CH:6]=[CH:5][C:4]=1[Cl:10].C/C(/[O-])=C/C(C)=O.C(OO)(C)(C)C>ClC1C=CC=CC=1>[Cl:10][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]([Cl:9])[C:3]=1[C:2]([P:11](=[O:24])([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:1]

Participants

5

Reactant 3

HCID 6410tert-Butyl hydroperoxideHCID 5460482AcetylacetonateHCID 10970858alpha-Hydroxy-(2,6-dichlorobenzyl)-diphenyl phosphine oxide

Product 1

HCID 109816492,6-Dichlorobenzoyl diphenylphosphine oxideYield 64%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

To 15 g (0.04 mol) of α-hydroxy-(2,6-dichorobenzyl)-diphenyl phosphine oxide and 0.4 g (1.5 mmol) of vanadyl(IV) bis-acetylacetonate in 100 g of chlorobenzene there were added 12.9 g (0.1 mol) 70 wt % strength aqueous tert-butylhydroperoxide, and the mixture was kept at 70° C. for 5 h. The product was isolated by crystallization. Yield: 64%, mp 156°-158° C.

Workup

  1. customThe product was isolated by crystallization

Sources & evidence

ORD record
ord-33bebe2b55134f9dba1197f54d164f89
Source dataset
uspto-grants-1997_10
Patent number
US05679863

Reaction notes

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