Water → Di-[1-(alpha-methylbenzyloxy)-2,2,6,6-tetramethylpiperidine-4-yl] Sebacate

HRID 1650025Notes

Reaction equation

HRID 1650025 reaction equation
[C:1]([O:24][CH:25]1[CH2:30][C:29]([CH3:32])([CH3:31])[NH:28][C:27]([CH3:34])([CH3:33])[CH2:26]1)(=[O:23])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([O:12][CH:13]1[CH2:18][C:17]([CH3:20])([CH3:19])[NH:16][C:15]([CH3:22])([CH3:21])[CH2:14]1)=[O:11].[C:35]([O:39]O)([CH3:38])([CH3:37])C.[OH2:41].[CH2:42]([C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)[CH3:43]>[Mo](=O)(=O)=O>[C:1]([O:24][CH:25]1[CH2:30][C:29]([CH3:32])([CH3:31])[N:28]([O:41][CH:42]([CH3:43])[C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[C:27]([CH3:34])([CH3:33])[CH2:26]1)(=[O:23])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([O:12][CH:13]1[CH2:18][C:17]([CH3:19])([CH3:20])[N:16]([O:39][CH:35]([CH3:38])[C:37]2[CH:5]=[CH:4][CH:3]=[CH:2][CH:1]=2)[C:15]([CH3:21])([CH3:22])[CH2:14]1)=[O:11]

Participants

6

Reactant 4

HCID 962WaterHCID 6410tert-Butyl hydroperoxideHCID 7500EthylbenzeneHCID 164282Tinuvin 770

Product 1

HCID 19768362Di-[1-(alpha-methylbenzyloxy)-2,2,6,6-tetramethylpiperidine-4-yl] SebacateYield 70%

Reagents, catalysts & solvents 1

HCID 14802Molybdenum trioxideCatalyst

Conditions

Temperature
110 °C

Procedure

A mixture of 40.0 g (83 mmol) of di-(2,2,6,6-tetramethylpiperidin-4-yl) sebacate, 2.0 g of molybdenum trioxide, and 250 ml of ethylbenzene is heated to 110° C. (nitrogen atmosphere). A commercially available solution of 70% t-butyl hydroperoxide in water (64.3 g, 499 mmol) is added dropwise over 30 min. Water is collected in a Dean-Stark trap. Heating is continued for 90 minutes after the addition. The reaction mixture is filtered and evaporated. The resulting crude oil is dissolved in heptane (300 ml), and this solution is passed through a short column of silica gel. The first 350 ml of filtrate, nearly pure by TLC, is evaporated to give 41.7 g (70% yield) of the title compound, a viscous oil.

Workup

  1. customWater is collected in a Dean-Stark trap
  2. temperatureHeating
  3. additionafter the addition
  4. filtrationThe reaction mixture is filtered
  5. customevaporated
  6. dissolutionThe resulting crude oil is dissolved in heptane (300 ml)
  7. customThe first 350 ml of filtrate, nearly pure by TLC, is evaporated

Sources & evidence

ORD record
ord-49873674d1ee4840ab8b064d4f008e00
Source dataset
uspto-grants-1990_05
Patent number
US04921962

Reaction notes

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