tert-Butyl hydroperoxide → Di-(1-heptyloxy-2,2,6,6-tetramethylpiperidin-4-yl) Sebacate

HRID 2050991Notes

Reaction equation

HRID 2050991 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])(C)C>[Mo](=O)(=O)=O.CCCCCCC>[C:1]([O:24][CH:25]1[CH2:30][C:29]([CH3:32])([CH3:31])[N:28]([O:39][CH2:35][CH2:38][CH2:17][CH2:18][CH2:13][CH2:14][CH3:15])[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:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH3:4])[C:15]([CH3:21])([CH3:22])[CH2:14]1)=[O:11]

Participants

5

Reactant 2

HCID 6410tert-Butyl hydroperoxide2×HCID 164282Tinuvin 770

Product 1

HCID 50943158Di-(1-heptyloxy-2,2,6,6-tetramethylpiperidin-4-yl) SebacateYield 72%

Reagents, catalysts & solvents 2

HCID 14802Molybdenum trioxideCatalystHCID 8900HeptaneSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 35.0 g (72.8 mmol) of di-(2,2,6,6-tetramethylpiperidin-4-yl) sebacate, 58.3 (582 mmol) of 90% aqueous t-butyl hydroperoxide, 2.0 g of molybdenum trioxide, and 250 ml of heptane is heated at 140° C. in a Fischer-Porter bottle. The pressure is maintained at 40-50 psi by occasional venting. Heating is discontinued after 7 hours. An additional portion (20.0 g) of 90% t-butyl hydroperoxide is added and the reaction mixture is heated for one hour at 140° C. The reaction is nearly colorless by this time. The reaction mixture is cooled and filtered to remove the catalyst. The organic phase is separated, dried over magnesium sulfate, and concentrated to 100 ml total volume. This solution is passed through silica gel with heptane as the eluent. The filtrate is evaporated to yield 36.9 g (72% yield) of di-(1-heptyloxy-2,2,6,6-tetramethylpiperidin-4-yl) sebacate, a nearly colorless oil. Elution of the column with 10:1 heptane:ethyl acetate then affords the title compound as a mixture of heptanediyl isomers.

Workup

  1. temperatureThe pressure is maintained at 40-50 psi by occasional venting
  2. temperatureHeating
  3. temperaturethe reaction mixture is heated for one hour at 140° C
  4. temperatureThe reaction mixture is cooled
  5. filtrationfiltered
  6. customto remove the catalyst
  7. customThe organic phase is separated
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated to 100 ml total volume
  10. customThe filtrate is evaporated

Sources & evidence

ORD record
ord-5fca0fcdf5774226813874bfe709af2a
Source dataset
uspto-grants-1991_05
Patent number
US05015682

Reaction notes

Loading…