tert-Butanol → beta-Methylenephenethyl alcohol

HRID 17783

反応式

HRID 17783 の反応式
CC[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[C:11]([OH:15])(C)(C)C.[Se](=O)=O.C1(C(C)=C)C=CC=CC=1>C(Cl)Cl.C(O)(=O)C>[OH:15][CH2:11][C:9]([C:8]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[CH2:10]

参加物

7

反応物 4

HCID 6386tert-ButanolHCID 7407Alpha-MethylstyreneHCID 15600DecaneHCID 24007Selenium Dioxide

生成物 1

HCID 80106beta-Methylenephenethyl alcohol収率 59%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 6344Dichloromethane溶媒

実験手順

A 12.5 ml of decane solution of 5 to 6 mol/L of per-tert-butylalcohol is diluted with 50 ml of methylene chloride, then 111 mg of selenium dioxide and 90.1 mg of an acetic acid were added thereto to react while stirring at room temperature for 30 min. Then, 6.5 ml of 2-phenylpropene was added to the reaction solution to react while stirring for 72 hours, followed by condensation under reduced pressure, and purification by silica gel column chromatography to obtain 3.98 g of 3-hydroxy-2-phenylpropene (yield: 59%). Measurement results by 1H-NMR and 13C-NMR of 3-hydroxy-2-phenylpropene obtained are shown below.

後処理

  1. customto react
  2. customto react
  3. stirringwhile stirring for 72 hours
  4. customfollowed by condensation under reduced pressure, and purification by silica gel column chromatography

出典と根拠

ORDレコード
ord-19597bdefb3548119f1a52e9b0ae7935
出典データセット
uspto-grants-2010_06
特許番号
US07741242B2

関連ノート

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