Water → Bis(1-cyclooctyloxy-2,2,6,6-tetramethylpiperidin-4-yl)sebacate

HRID 1650042Notes

Reaction equation

HRID 1650042 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].[CH2:35]1[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1.[C:43]([O:47]O)(C)([CH3:45])[CH3:44].[OH2:49]>[Mo](=O)(=O)=O>[C:1]([O:24][CH:25]1[CH2:30][C:29]([CH3:32])([CH3:31])[N:28]([O:47][CH:43]2[CH2:45][CH2:5][CH2:4][CH2:3][CH2:2][CH2:1][CH2:44]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:49][CH:35]2[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]2)[C:15]([CH3:21])([CH3:22])[CH2:14]1)=[O:11]

Participants

6

Reactant 4

HCID 962WaterHCID 6410tert-Butyl hydroperoxideHCID 9266CyclooctaneHCID 164282Tinuvin 770

Product 1

HCID 19768323Bis(1-cyclooctyloxy-2,2,6,6-tetramethylpiperidin-4-yl)sebacateYield 68%

Reagents, catalysts & solvents 1

HCID 14802Molybdenum trioxideCatalyst

Conditions

Temperature
118 °C

Procedure

A mixture of 75 g (156 mmol) of di-(2,2,6,6-tetramethylpiperidin-4-yl) sebacate, 1.3 g of molybdenum trioxide and 475 ml of cyclooctane is heated to 118° C. To this mixture is added 130 g (1.01 mol) of 70% aqueous tert-butyl hydroperoxide during a 5-hour period. The reaction mixture is maintained at reflux during the addition period, and water is collected in a Dean-Stark trap. The red reaction mixture is heated at reflux for 7 hours after the addition is complete to discharge the red color. The solids are removed by filtration and the filtrate is evaporated to give a yellow oil. Purification (Waters Prep 500A HPLC, 20:1 hexane:ethyl acetate) affords 78.7 g (68% yield) of the title compound as a colorless syrup.

Workup

  1. temperatureThe reaction mixture is maintained
  2. customis collected in a Dean-Stark trap
  3. customThe red reaction mixture
  4. temperatureis heated
  5. temperatureat reflux for 7 hours
  6. additionafter the addition
  7. customThe solids are removed by filtration
  8. customthe filtrate is evaporated
  9. customto give a yellow oil
  10. customPurification (Waters Prep 500A HPLC, 20:1 hexane:ethyl acetate)

Sources & evidence

ORD record
ord-ce854cc29184450f89d68e088062edd6
Source dataset
uspto-grants-1990_05
Patent number
US04921962

Reaction notes

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