Water → HCID 17846597, compound

HRID 1650027Notes

Reaction equation

HRID 1650027 reaction equation
[C:1]([O:22][CH:23]1[CH2:28][C:27]([CH3:30])([CH3:29])[NH:26][C:25]([CH3:32])([CH3:31])[CH2:24]1)(=[O:21])[C:2]1[CH:20]=[CH:19][C:5]([C:6]([O:8][CH:9]2[CH2:14][C:13]([CH3:16])([CH3:15])[NH:12][C:11]([CH3:18])([CH3:17])[CH2:10]2)=[O:7])=[CH:4][CH:3]=1.[CH2:33]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[CH3:34].[C:41]([O:45]O)(C)([CH3:43])[CH3:42].[OH2:47]>[Mo](=O)(=O)=O>[C:6]([O:8][CH:9]1[CH2:10][C:11]([CH3:18])([CH3:17])[N:12]([O:45][CH:41]([CH3:43])[C:42]2[CH:19]=[CH:20][CH:2]=[CH:3][CH:4]=2)[C:13]([CH3:15])([CH3:16])[CH2:14]1)(=[O:7])[C:5]1[CH:4]=[CH:3][C:2]([C:1]([O:22][CH:23]2[CH2:24][C:25]([CH3:32])([CH3:31])[N:26]([O:47][CH:33]([CH3:34])[C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[C:27]([CH3:30])([CH3:29])[CH2:28]2)=[O:21])=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6410tert-Butyl hydroperoxideHCID 7500EthylbenzeneHCID 14618559HCID 14618559, compound

Product 1

HCID 17846597HCID 17846597, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 14802Molybdenum trioxideCatalyst

Procedure

A suspension of 40.0 g (90.0 mmol) of di-(2,2,6,6-tetramethylpiperidin-4-yl) terephthalate, 2.0 g of molybdenum trioxide, and 250 ml of ethylbenzene is heated to 110° C. t-Butyl hydroperoxide (70%, 69.5 g, 540 mmol) is rapidly added. No reaction is visible until water is removed by azeotropic distillation and the internal temperature reaches 115° C. Heating is continued for 6 hours. The nearly colorless reaction mixture is allowed to cool, then filtered and evaporated to yield a pink solid. The solid is recrystallized (9:1 2-propanol:methylene chloride) to yield 48.4 g of the title compound, a white solid, m.p. 150°-152° C. A second crop of 5.3 g is obtained from the mother liquor. Total yield 53.7 g (87% yield).

Workup

  1. additionis rapidly added
  2. customis removed by azeotropic distillation
  3. customreaches 115° C
  4. temperatureHeating
  5. temperatureto cool
  6. filtrationfiltered
  7. customevaporated
  8. customto yield a pink solid
  9. customThe solid is recrystallized (9:1 2-propanol:methylene chloride)

Sources & evidence

ORD record
ord-229171a377854cf8a74b57ca263cb238
Source dataset
uspto-grants-1990_05
Patent number
US04921962

Reaction notes

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