Sodium Chloride → Di-[1-(1-Methylcyclohexyloxy)-2,2,6,6-tetramethylpiperidin-4-yl] Sebacate

HRID 1650034Notes

Reaction equation

HRID 1650034 reaction equation
[C:1]([O:5]O)([CH3:4])([CH3:3])[CH3:2].[Cl-].[Na+].[C:9]([O:32][CH:33]1[CH2:38][C:37]([CH3:40])([CH3:39])[NH:36][C:35]([CH3:42])([CH3:41])[CH2:34]1)(=[O:31])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][CH:21]1[CH2:26][C:25]([CH3:28])([CH3:27])[NH:24][C:23]([CH3:30])([CH3:29])[CH2:22]1)=[O:19]>[Mo](=O)(=O)=O.CC1CCCCC1>[C:9]([O:32][CH:33]1[CH2:38][C:37]([CH3:40])([CH3:39])[N:36]([O:5][C:1]2([CH3:4])[CH2:3][CH2:14][CH2:13][CH2:12][CH2:2]2)[C:35]([CH3:42])([CH3:41])[CH2:34]1)(=[O:31])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][CH:21]1[CH2:26][C:25]([CH3:27])([CH3:28])[N:24]([O:5][C:1]2([CH3:4])[CH2:3][CH2:11][CH2:10][CH2:9][CH2:2]2)[C:23]([CH3:29])([CH3:30])[CH2:22]1)=[O:19]

Participants

6

Reactant 3

HCID 5234Sodium ChlorideHCID 6410tert-Butyl hydroperoxideHCID 164282Tinuvin 770

Product 1

HCID 19768333Di-[1-(1-Methylcyclohexyloxy)-2,2,6,6-tetramethylpiperidin-4-yl] SebacateYield 140.7%

Reagents, catalysts & solvents 2

HCID 14802Molybdenum trioxideCatalystHCID 7962MethylcyclohexaneSolvent2×

Procedure

t-Butyl hydroperoxide (70%, 133.9 g, 1.04 mol), methylcyclohexane (250 ml), and sodium chloride (20 g) are agitated in a separatory funnel. The organic layer is dried over magnesium sulfate. The t-butyl hydroperoxidemethylcyclohexane solution is mixed with 50.0 g (104 mmol) of di-(2,2,6,6-tetramethylpiperidin-4-yl) sebacate, 3.0 g of molybdenum trioxide, and 100 ml of methylcyclohexane. The reaction mixture is heated at reflux for 4.5 hours and water is collected in a Dean-Stark trap. The reaction is cooled to room temperature and filtered. The filtrate is concentrated at reduced pressure to obtain an oil which is purified by flash chromatography (silica gel; 19:1 heptane:ethyl acetate) to obtain 51.6 g (72% yield) of a colorless oil.

Workup

  1. dry with materialThe organic layer is dried over magnesium sulfate
  2. temperatureThe reaction mixture is heated
  3. temperatureat reflux for 4.5 hours
  4. customwater is collected in a Dean-Stark trap
  5. filtrationfiltered
  6. concentrationThe filtrate is concentrated at reduced pressure
  7. customto obtain an oil which
  8. customis purified by flash chromatography (silica gel; 19:1 heptane:ethyl acetate)

Sources & evidence

ORD record
ord-582f1cf8654940a18df83b254d017878
Source dataset
uspto-grants-1990_05
Patent number
US04921962

Reaction notes

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