tert-Butyl hydroperoxide → Bis(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl) sebacate

HRID 1590923

反応式

HRID 1590923 の反応式
[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])([CH3:37])C>[Mo](=O)(=O)=O.C1CCCCC1>[C:1]([O:24][CH:25]1[CH2:30][C:29]([CH3:32])([CH3:31])[N:28]([O:39][CH:35]2[CH2:38][CH2:6][CH2:5][CH2:4][CH2:37]2)[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:39][CH:35]2[CH2:38][CH2:3][CH2:2][CH2:1][CH2:37]2)[C:15]([CH3:21])([CH3:22])[CH2:14]1)=[O:11]

参加物

5

反応物 2

HCID 6410tert-Butyl hydroperoxideHCID 164282Tinuvin 770

生成物 1

HCID 18716452Bis(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl) sebacate収率 126.4%

試薬・触媒・溶媒 2

HCID 14802Molybdenum trioxide触媒HCID 8078Cyclohexane溶媒2 回

反応条件

温度
140 °C

実験手順

A mixture of 20.0 g (41.6 mmol) of di-(2,2,6,6-tetramethylpiperidin-4-yl) sebacate, 43 g (334 mmol) of 70% aqueous t-butyl hydroperoxide, 1.3 g (9.0 mmol) of molybdenum trioxide, and 125 ml of cyclohexane is heated at reflux for 2.3 hours. Water is collected in a Dean-Stark trap. The red reaction mixture is cooled and transferred to a Fischer-Porter bottle. Fresh cyclohexane (25 ml) is used to thoroughly rinse the flask, and the rinsings are added to the pressure bottle. The pressure bottle is immersed in an oil bath (140° C.) for 3 hours whereupon the colorless reaction mixture is cooled to room temperature and filtered. The filtrate is stirred with 10 g of sodium sulfite in 90 ml of water for 2 hours to decompose unreacted hydroperoxide, then diluted with ethyl acetate (200 ml) and water (100 ml). The organic layer is washed with 10% sodium sulfite (100 ml), water (100 ml), saturated sodium chloride (100 ml), then dried over magnesium sulfate and concentrated at reduced pressure. The crude product is purified by flash chromatography (silica gel, 100:2 heptane:ethyl acetate) to afford 17.8 g (63% yield) of a white solid, m.p. 56°-9° C.

後処理

  1. temperatureis heated
  2. temperatureat reflux for 2.3 hours
  3. customWater is collected in a Dean-Stark trap
  4. customThe red reaction mixture
  5. temperatureis cooled
  6. washto thoroughly rinse the flask
  7. additionthe rinsings are added to the pressure bottle
  8. customThe pressure bottle is immersed in an oil bath
  9. filtrationfiltered
  10. additiondiluted with ethyl acetate (200 ml) and water (100 ml)
  11. washThe organic layer is washed with 10% sodium sulfite (100 ml), water (100 ml), saturated sodium chloride (100 ml)
  12. dry with materialdried over magnesium sulfate
  13. concentrationconcentrated at reduced pressure
  14. customThe crude product is purified by flash chromatography (silica gel, 100:2 heptane:ethyl acetate)

出典と根拠

ORDレコード
ord-7479402140c5472bbb315cb2b14abab2
出典データセット
uspto-grants-1993_04
特許番号
US05204473

関連ノート

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