Hydrogen Peroxide → 1-(2-Methyl-2-phenylpropyloxy)-4-benzoyloxy-2,2,6,6-tetramethylpiperidine

HRID 133635

反応式

HRID 133635 の反応式
[OH:1][N:2]1[C:7]([CH3:9])([CH3:8])[CH2:6][CH:5]([O:10][C:11](=[O:18])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:4][C:3]1([CH3:20])[CH3:19].[C:21]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([CH3:24])([CH3:23])[CH3:22].OO.S([O-])([O-])=O.[Na+].[Na+]>O.C(OCC)(=O)C.CCCCCCC.C(OCC)(=O)C.C(#N)C>[CH3:22][C:21]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([CH3:24])[CH2:23][O:1][N:2]1[C:7]([CH3:9])([CH3:8])[CH2:6][CH:5]([O:10][C:11](=[O:18])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:4][C:3]1([CH3:20])[CH3:19]

参加物

9

反応物 4

HCID 784Hydrogen PeroxideHCID 7366Tert-ButylbenzeneHCID 24437Sodium SulfiteHCID 6881781-Hydroxy-4-benzoyloxy-2,2,6,6-tetramethylpiperidine

生成物 1

HCID 509433191-(2-Methyl-2-phenylpropyloxy)-4-benzoyloxy-2,2,6,6-tetramethylpiperidine収率 10%

試薬・触媒・溶媒 4

HCID 962Water溶媒HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒HCID 21899848Ethylacetate heptane溶媒

反応条件

温度
61 °C

実験手順

A solution of 0.077 g (0.39 mmol) of ferrous chloride tetrahydrate in 2.2 g of water is added to a mixture of 5.00 g (18.1 mmol) of 1-oxyl-4-benzoyloxy-2,2,6,6-tetramethylpiperidine, 16 ml of t-butylbenzene, and 28 ml of acetonitrile that has been heated to 61° C. A solution of 5.03 g (74 mmol) of 50% aqueous hydrogen peroxide is added dropwise over 2 hours to the reaction mixture while the temperature is maintained at 65°. After the peroxide is added, the mixture is stirred for 1.25 hours at 65°. The reaction mixture is cooled to 30° and stirred with 20 ml of 10% aqueous sodium sulfite solution to decompose excess peroxide. The crude reaction mixture is diluted with ethyl acetate, and the organic layer is concentrated. Purification by flash chromatography with 100:1 and then 25:1 heptane-ethyl acetate affords 0.75 g (10% yield) of the title compound, a pale yellow oil. Structure is confirmed by NMR and mass spectrometry.

後処理

  1. temperatureis maintained at 65°
  2. temperatureThe reaction mixture is cooled to 30°
  3. customThe crude reaction mixture
  4. concentrationthe organic layer is concentrated
  5. customPurification by flash chromatography with 100:1

出典と根拠

ORDレコード
ord-65797e4d9e274a65a671df67f91a19a5
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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