Hydrogen Peroxide → 1-Cyclohexyloxy-4-benzoyloxy-2,2,6,6-tetramethylpiperidine

HRID 133645

反応式

HRID 133645 の反応式
B(O)(O)O.[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].[C:25](#N)[CH3:26].OO>O.B(O)(O)O.C1CCCCC1>[CH:26]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])[CH2:25][CH2:9][CH2:8][CH2:7][CH2:23]1

参加物

8

反応物 4

HCID 784Hydrogen PeroxideHCID 6342AcetonitrileHCID 7628Boric AcidHCID 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 68%

試薬・触媒・溶媒 3

HCID 7628Boric Acid触媒HCID 962Water溶媒2 回HCID 8078Cyclohexane溶媒

反応条件

温度
52 °C

実験手順

A solution of 0.100 g (0.360 mmol) of ferrous sulfate heptahydrate and 0.112 g (1.82 mmol) of boric acid in 4 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 acetonitrile, and 19 ml of cyclohexane. The mixture is heated to 52° C. A solution of 4.98 g (73 mmol) of 50% aqueous hydrogen peroxide is added dropwise over 2.75 hours to the reaction mixture while the temperature is brought to and maintained at reflux (63° C.). A solution of 0.051 g of ferrous sulfate heptahydrate and 0.042 g of boric acid in 2 ml of water is added to the reaction mixture 1.25 hours after the peroxide addition is started. After the peroxide is added, the reaction mixture is heated at reflux for 30 minutes, then allowed to cool slowly. Work-up and purification according to the procedure of Example 5 afford 4.42 g (68% yield) of the title compound, a colorless syrup, GC assay 99.3%.

後処理

  1. temperaturemaintained
  2. temperatureat reflux (63° C.)
  3. temperaturethe reaction mixture is heated
  4. temperatureat reflux for 30 minutes
  5. temperatureto cool slowly
  6. custompurification

出典と根拠

ORDレコード
ord-3be2a870370043d3af12d94d8a753174
出典データセット
uspto-grants-2008_06
特許番号
US07390904B2

関連ノート

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