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

HRID 133644

反応式

HRID 133644 の反応式
[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

参加物

7

反応物 5

HCID 176Acetic AcidHCID 784Hydrogen Peroxide2 回HCID 887MethanolHCID 962WaterHCID 6881781-Hydroxy-4-benzoyloxy-2,2,6,6-tetramethylpiperidine

生成物 1

HCID 233720981-Cyclohexyloxy-4-benzoyloxy-2,2,6,6-tetramethylpiperidine収率 40%

試薬・触媒・溶媒 1

HCID 8078Cyclohexane溶媒

反応条件

温度
55 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-d30f20b90bff4edb90586a46d73f3455
出典データセット
uspto-grants-2008_06
特許番号
US07390904B2

関連ノート

読み込み中…