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

HRID 1650031

반응식

HRID 1650031 반응식
[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]

참가 물질

6

반응물 3

HCID 5234Sodium ChlorideHCID 6410tert-Butyl hydroperoxide2회HCID 93340Bis(2,2,6,6-tetramethyl-4-piperidyl) succinate

생성물 1

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

시약·촉매·용매 2

HCID 14802Molybdenum trioxide촉매HCID 8078Cyclohexane용매

반응 조건

온도
140 °C

실험 절차

A two-phase mixture of 70% aqueous t-butyl hydroperoxide (103.9 g, 807 mmol), cyclohexane (200 ml) and sodium chloride (15 g) is shaken in a separatory funnel. The organic phase is dried over magnesium sulfate, filtered, and added to 40.0 g (101 mmol) of di-(2,2,6,6-tetramethylpiperidin-4-yl) succinate. Molybdenum trioxide (2.0 g) is added, and the mixture is refluxed for one hour. Water is collected in a Dean-Stark trap. The entire reaction mixture is then transferred to a Fischer-Porter bottle and heated at 140° C. for 6 hours. Additional t-butyl hydroperoxide (90%, 10.1 g, 101 mmol) is added and heating is resumed for another 4 hours. The colorless reaction mixture is filtered, concentrated, and dissolved in heptane (200 ml). The heptane solution is passed through a short column of silica gel with heptane. Subsequent evaporation affords an oil which is crystallized from ethanol to yield 41.2 g (69%) of a white powder, m.p. 122°-6° C.

후처리

  1. dry with materialThe organic phase is dried over magnesium sulfate
  2. filtrationfiltered
  3. temperaturethe mixture is refluxed for one hour
  4. customWater is collected in a Dean-Stark trap
  5. customThe entire reaction mixture
  6. temperatureheating
  7. filtrationThe colorless reaction mixture is filtered
  8. concentrationconcentrated
  9. dissolutiondissolved in heptane (200 ml)
  10. customSubsequent evaporation
  11. customaffords an oil which
  12. customis crystallized from ethanol

출처 및 근거

ORD 기록
ord-d3912e21d51f4a29badcf37cec627249
출처 데이터셋
uspto-grants-1990_05
특허 번호
US04921962

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