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

HRID 1590943

반응식

HRID 1590943 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 14802Molybdenum trioxide촉매HCID 7962Methylcyclohexane용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-11708737ad92458586bfb04c20f93784
출처 데이터셋
uspto-grants-1993_04
특허 번호
US05204473

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