tert-Butyl hydroperoxide → (3-Chloro-2,4,6-trimethylbenzoyl)diphenylphosphine oxide

HRID 1720114

Reaction equation

HRID 1720114 reaction equation
[OH:1][CH:2]([P:13](=[O:26])([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:3]1[C:8]([CH3:9])=[CH:7][C:6]([CH3:10])=[C:5]([Cl:11])[C:4]=1[CH3:12].C/C(/[O-])=C/C(C)=O.C(OO)(C)(C)C>ClC1C=CC=CC=1.[O-][V]([O-])([O-])=O.[Na+].[Na+].[Na+]>[Cl:11][C:5]1[C:4]([CH3:12])=[C:3]([C:8]([CH3:9])=[CH:7][C:6]=1[CH3:10])[C:2]([P:13](=[O:26])([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)=[O:1]

Participants

6

Reactant 3

HCID 6410tert-Butyl hydroperoxideHCID 5460482AcetylacetonateHCID 86749383alpha-Hydroxy-(3-chloro-2,4,6-trimethylbenzyl)-diphenyl phosphine oxide

Product 1

HCID 22420311(3-Chloro-2,4,6-trimethylbenzoyl)diphenylphosphine oxideYield 81%

Reagents, catalysts & solvents 2

HCID 61671Sodium orthovanadateCatalystHCID 7964ChlorobenzeneSolvent

Procedure

To 15.4 g (0.04 mol) of α-hydroxy-(3-chloro-2,4,6-trimethylbenzyl)-diphenyl phosphine oxide and 0.4 S (1.5mmol) of vanadyl (IV) bis-acetylacetonate in 100 g of chlorobenzene there were added 8.2 g (0.06 mol) of 70w t% strength aqueous tert-butylhydroperoxide and isolated by crystallization following a period of 20 h. Yield: 81%, mp 125°-126° C.

Workup

  1. customisolated by crystallization

Sources & evidence

ORD record
ord-c6407c3bd2cd4c85aaffa930feb700ae
Source dataset
uspto-grants-1996_04
Patent number
US05504236

Linked notes

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