tert-Butyl hydroperoxide → 4-Acetamido-1-cyclohexyloxy-2,2,6,6-tetramethylpiperidine

HRID 1590946ノート

反応式

HRID 1590946 の反応式
[CH3:1][C:2]([NH:4][CH:5]1[CH2:10][C:9]([CH3:12])([CH3:11])[N:8]([O])[C:7]([CH3:15])([CH3:14])[CH2:6]1)=[O:3].[C:16]([O:20]O)(C)([CH3:18])[CH3:17].[CH2:22]1[CH2:27]CCC[CH2:23]1>[Mo](=O)(=O)=O>[C:2]([NH:4][CH:5]1[CH2:10][C:9]([CH3:12])([CH3:11])[N:8]([O:20][CH:16]2[CH2:18][CH2:27][CH2:22][CH2:23][CH2:17]2)[C:7]([CH3:15])([CH3:14])[CH2:6]1)(=[O:3])[CH3:1]

参加物

5

反応物 3

HCID 6410tert-Butyl hydroperoxideHCID 8078CyclohexaneHCID 5189884-Acetamido-TEMPO

生成物 1

HCID 233721204-Acetamido-1-cyclohexyloxy-2,2,6,6-tetramethylpiperidine

試薬・触媒・溶媒 1

HCID 14802Molybdenum trioxide触媒

反応条件

温度
140 °C

実験手順

A stirred mixture of 10.0 g of 4-acetamido-2,2,6,6-tetramethylpiperidine-1-oxyl, 16 ml of 70% aqueous tert-butylhydroperoxide and 0.67 g of molybdenum trioxide in 75 ml of cyclohexane is heated under reflux in a flask fitted with a Dean-Stark apparatus. After 6 ml of water is collected, the reaction mixture is transferred to a Fisher Porter apparatus and heated at 140° C. and 30 psi for 4 hours. The decolorized reaction mixture is filtered and the filtrate is washed with water, aqueous sodium sulfite, brine, dried (MgSO4) and concentrated to give 13.61 g of a white solid. Recrystallization from heptane affords 10.39 g of the title compound as a white crystalline solid, m.p. 140°-44° C.

後処理

  1. temperatureis heated
  2. temperatureunder reflux in a flask
  3. customfitted with a Dean-Stark apparatus
  4. customAfter 6 ml of water is collected
  5. customThe decolorized reaction mixture
  6. filtrationis filtered
  7. washthe filtrate is washed with water, aqueous sodium sulfite, brine
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-84b88c07723a4a56b68009f22fc110ed
出典データセット
uspto-grants-1993_04
特許番号
US05204473

反応ノート

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