Sodium Chloride → Bis(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl) succinate

HRID 2050993

Reaction equation

HRID 2050993 reaction equation
[C:1]([O:5]O)([CH3:4])([CH3:3])C.[Cl-].[Na+].[C:9]([O:26][CH:27]1[CH2:32][C:31]([CH3:34])([CH3:33])[NH:30][C:29]([CH3:36])([CH3:35])[CH2:28]1)(=[O:25])[CH2:10][CH2:11][C:12]([O:14][CH:15]1[CH2:20][C:19]([CH3:22])([CH3:21])[NH:18][C:17]([CH3:24])([CH3:23])[CH2:16]1)=[O:13]>[Mo](=O)(=O)=O.C1CCCCC1>[C:9]([O:26][CH:27]1[CH2:32][C:31]([CH3:34])([CH3:33])[N:30]([O:5][CH:1]2[CH2:4][CH2:20][CH2:15][CH2:16][CH2:3]2)[C:29]([CH3:36])([CH3:35])[CH2:28]1)(=[O:25])[CH2:10][CH2:11][C:12]([O:14][CH:15]1[CH2:16][C:17]([CH3:24])([CH3:23])[N:18]([O:5][CH:1]2[CH2:4][CH2:11][CH2:10][CH2:9][CH2:3]2)[C:19]([CH3:22])([CH3:21])[CH2:20]1)=[O:13]

Participants

6

Reactant 3

HCID 5234Sodium ChlorideHCID 6410tert-Butyl hydroperoxide2×HCID 93340Bis(2,2,6,6-tetramethyl-4-piperidyl) succinate

Product 1

HCID 21026400Bis(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl) succinateYield 137.6%

Reagents, catalysts & solvents 2

HCID 14802Molybdenum trioxideCatalystHCID 8078CyclohexaneSolvent

Conditions

Temperature
140 °C

Procedure

A two-phase mixture of 70% aqueous tert-butyl hydroperoxide (103.9 grams, 807 mmol), cyclohexane (200 ml) and sodium chloride (15 grams) is shaken in a separatory funnel. The organic phase is dried over anhydrous magnesium sulfate, filtered and added to 40 grms (101 mmol) of bis(2,2,6,6-tetramethylpiperidin-4-yl) succinate. Molybdenum trioxide (2.0 grams) is added and the mixture is heated at reflux for one hour. Water is collected in a Dean-Stark trap. The entire reaction mixture is then transferred to a Fischer-Porter pressure bottle and heated for six hours at 140° C. Additional tert-butyl hydroperoxide (90%, 10.1 grams, 101 mmol) is added and heating is resumed for another four hours. The colorless reaction mixture is filtered, concentrated and dissolved in heptane (200 ml). The heptane solution is passed through a column of silica gel with heptane as the eluent to obtrain 41.2 grams (69% yield) of bis(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl) succinate as a white solid melting at 122-126° C. Further elution of the column with 10:1 heptane:ethyl acetate affords the title compound as a mixture of cyclohexanediyl isomers.

Workup

  1. dry with materialThe organic phase is dried over anhydrous magnesium sulfate
  2. filtrationfiltered
  3. temperaturethe mixture is heated
  4. temperatureat reflux for one hour
  5. customWater is collected in a Dean-Stark trap
  6. customThe entire reaction mixture
  7. temperatureheating
  8. filtrationThe colorless reaction mixture is filtered
  9. concentrationconcentrated
  10. dissolutiondissolved in heptane (200 ml)

Sources & evidence

ORD record
ord-42a3961cd5d143c0a582000de5c84ccd
Source dataset
uspto-grants-1991_05
Patent number
US05015682

Linked notes

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