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

HRID 1590934

반응식

HRID 1590934 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.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 139765Molybdenum oxide촉매HCID 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 oxide (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 (20 0 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 (20 0 ml)
  10. customSubsequent evaporation
  11. customaffords an oil which
  12. customis crystallized from ethanol

출처 및 근거

ORD 기록
ord-a1480b7fb3654dbca29483403b9b58c6
출처 데이터셋
uspto-grants-1993_04
특허 번호
US05204473

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