Acetic Acid → 1-Cyclohexyloxy-4-benzoyloxy-2,2,6,6-tetramethylpiperidine

HRID 133644

반응식

HRID 133644 반응식
[C:1](O)(=O)[CH3:2].[OH:5][N:6]1[C:11]([CH3:13])([CH3:12])[CH2:10][CH:9]([O:14][C:15](=[O:22])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:8][C:7]1([CH3:24])[CH3:23].CO.OO.O>C1CCCCC1>[CH:2]1([O:5][N:6]2[C:11]([CH3:13])([CH3:12])[CH2:10][CH:9]([O:14][C:15](=[O:22])[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:8][C:7]2([CH3:24])[CH3:23])[CH2:1][CH2:9][CH2:8][CH2:7][CH2:23]1

참가 물질

7

반응물 5

HCID 176Acetic AcidHCID 784Hydrogen Peroxide2회HCID 887MethanolHCID 962WaterHCID 6881781-Hydroxy-4-benzoyloxy-2,2,6,6-tetramethylpiperidine

생성물 1

HCID 233720981-Cyclohexyloxy-4-benzoyloxy-2,2,6,6-tetramethylpiperidine수율 40%

시약·촉매·용매 1

HCID 8078Cyclohexane용매

반응 조건

온도
55 °C

실험 절차

A solution of 0.101 g (0.37 mmol) of ferric chloride hexahydrate and 0.115 g (1.9 mmol) of glacial acetic acid in 2 ml of water is added to a mixture of 5.00 g (18.1 mmol) of 1-oxyl-4-benzoyloxy-2,2,6,6-tetramethylpiperidine, 27 ml of methanol, and 18 ml of cyclohexane. The mixture is heated to reflux, 55° C. A solution of 4.9 g (72 mmol) of 50% aqueous hydrogen peroxide is added dropwise over 2.25 hours to the reaction mixture while the temperature is brought to and maintained at reflux. After the peroxide is added, the reaction mixture tests negative for hydrogen peroxide. The yield of the title compound, after work-up with ethyl acetate and purification by flash chromatography, is 2.63 g (40% yield, GC assay 100%).

후처리

  1. temperatureThe mixture is heated
  2. temperaturemaintained
  3. temperatureat reflux
  4. customThe yield of the title compound, after work-up with ethyl acetate and purification by flash chromatography

출처 및 근거

ORD 기록
ord-d30f20b90bff4edb90586a46d73f3455
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07390904B2

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