tert-Butyl hydroperoxide → Tinuvin 123

HRID 1650037

반응식

HRID 1650037 반응식
[C:1]([O:5]O)([CH3:4])(C)C.[C:7]([O:30][CH:31]1[CH2:36][C:35]([CH3:38])([CH3:37])[NH:34][C:33]([CH3:40])([CH3:39])[CH2:32]1)(=[O:29])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([O:18][CH:19]1[CH2:24][C:23]([CH3:26])([CH3:25])[NH:22][C:21]([CH3:28])([CH3:27])[CH2:20]1)=[O:17]>[Mo](=O)(=O)=O.CCCCCCCC>[C:7]([O:30][CH:31]1[CH2:36][C:35]([CH3:38])([CH3:37])[N:34]([O:5][CH2:1][CH2:4][CH2:27][CH2:21][CH2:20][CH2:19][CH2:24][CH3:23])[C:33]([CH3:40])([CH3:39])[CH2:32]1)(=[O:29])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([O:18][CH:19]1[CH2:24][C:23]([CH3:25])([CH3:26])[N:22]([O:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH3:9])[C:21]([CH3:27])([CH3:28])[CH2:20]1)=[O:17]

참가 물질

5

반응물 2

HCID 6410tert-Butyl hydroperoxideHCID 164282Tinuvin 770

생성물 1

HCID 3592789Tinuvin 123수율 160.5%

시약·촉매·용매 2

HCID 14802Molybdenum trioxide촉매HCID 356Octane용매

반응 조건

온도
115 °C

실험 절차

70% Aqueous tert-butyl hydroperoxide (140 g, 1.09 mol) is added over a 6-hour period to a mixture of 75.4 g (0.157 mol) of bis(2,2,6,6-tetramethylpiperidin-4-yl) sebacate, 1.25 g (8.7 mmol) of molybdenum trioxide and 570 ml of n-octane, that is first heated to 115° C., under a nitrogen atmosphere. During the addition, the reaction mixture is maintained at reflux. Water is collected in a Dean-Stark trap. Upon completion of the addition, the red reaction mixture is heated at reflux (95°-97° C.) for seven hours to discharge the red color. The molybdenum trioxide is removed by filtration. The yellow filtrate is stirred at ambient temperature for 30 minutes with 15 g of activated charcoal (DARCO) to remove some of the yellow color before being concentrated under reduced pressure. The crude product is purified by flash chromatography on silica gel (100:3 heptane:ethyl acetate) to afford 92.9 g (80% yield) of the title compound as a colorless oil.

후처리

  1. additionDuring the addition
  2. temperaturethe reaction mixture is maintained
  3. temperatureat reflux
  4. customWater is collected in a Dean-Stark trap
  5. additionUpon completion of the addition
  6. customthe red reaction mixture
  7. temperatureis heated
  8. temperatureat reflux (95°-97° C.) for seven hours
  9. customThe molybdenum trioxide is removed by filtration
  10. customto remove some of the yellow color
  11. concentrationbefore being concentrated under reduced pressure
  12. customThe crude product is purified by flash chromatography on silica gel (100:3 heptane:ethyl acetate)

출처 및 근거

ORD 기록
ord-e89ee52be7ca4ac3901581bda23aa2f7
출처 데이터셋
uspto-grants-1990_05
특허 번호
US04921962

연결된 노트

불러오는 중…