Ethylbenzene → HCID 19768358, compound

HRID 1650024Notes

Reaction equation

HRID 1650024 reaction equation
[C:1]([O:23][CH:24]1[CH2:29][C:28]([CH3:31])([CH3:30])[N:27]([OH:32])[C:26]([CH3:34])([CH3:33])[CH2:25]1)(=[O:22])[C:2]1[C:3](=[CH:18][CH:19]=[CH:20][CH:21]=1)[C:4]([O:6][CH:7]1[CH2:12][C:11]([CH3:14])([CH3:13])[N:10]([OH:15])[C:9]([CH3:17])([CH3:16])[CH2:8]1)=[O:5].[CH2:35]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[CH3:36].[O-]O>O.[Mo](=O)(=O)=O>[C:4]([O:6][CH:7]1[CH2:12][C:11]([CH3:13])([CH3:14])[N:10]([O:15][CH:35]([CH3:36])[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:9]([CH3:17])([CH3:16])[CH2:8]1)(=[O:5])[C:3]1[C:2](=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:1]([O:23][CH:24]1[CH2:29][C:28]([CH3:31])([CH3:30])[N:27]([O:32][CH:35]([CH3:36])[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:26]([CH3:34])([CH3:33])[CH2:25]1)=[O:22]

Participants

6

Reactant 3

HCID 7500EthylbenzeneHCID 18500Perhydroxyl radicalHCID 1222549HCID 1222549, compound

Product 1

HCID 19768358HCID 19768358, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 14802Molybdenum trioxideCatalystHCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

The compound is prepared from 40.0 g of di-(1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl) phthalate, 200 ml of ethylbenzene, and 2.0 g of molybdenum trioxide which are heated to 110° C. (nitrogen atmosphere). Thereafter, 65 g of 70% t-butyl hydroxperoxide in water is added dropwise over one hour. The reaction mixture is refluxed for 3 hours after the hydroperoxide addition is complete. The crude product is chromatographed on silica gel (9:1 hexane:ethyl acetate) to give 51.0 g (88% yield) of a soft glassy product.

Workup

  1. temperatureThe reaction mixture is refluxed for 3 hours
  2. customThe crude product is chromatographed on silica gel (9:1 hexane:ethyl acetate)

Sources & evidence

ORD record
ord-b75090b4055d4566ac67a3d83242eb47
Source dataset
uspto-grants-1990_05
Patent number
US04921962

Reaction notes

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