Salicylic Acid → 4-Hydroxy-2-(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-tetradecatetraenenitrile

HRID 1464469

反応式

HRID 1464469 の反応式
[OH:1]C1C=CC=CC=1C(O)=O.C(OO)(C)(C)C.[CH3:17][CH:18]([C:20](=[CH:23][CH:24]=[C:25]([CH3:37])[CH2:26][CH2:27][CH:28]=[C:29]([CH3:36])[CH2:30][CH2:31][CH:32]=[C:33]([CH3:35])[CH3:34])[C:21]#[N:22])[CH3:19]>C(Cl)Cl.[Se](=O)=O>[OH:1][C:24](=[C:25]([CH3:37])[CH2:26][CH2:27][CH:28]=[C:29]([CH3:36])[CH2:30][CH2:31][CH:32]=[C:33]([CH3:35])[CH3:34])[CH:23]=[C:20]([CH:18]([CH3:17])[CH3:19])[C:21]#[N:22]

参加物

6

反応物 3

HCID 338Salicylic AcidHCID 6410tert-Butyl hydroperoxideHCID 536571452-(1-Methylethyl)-5,9,13-trimethyl-2,4,8,12-tetradecatetraenenitrile

生成物 1

HCID 867472134-Hydroxy-2-(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-tetradecatetraenenitrile収率 317.6%

試薬・触媒・溶媒 2

HCID 24007Selenium Dioxide触媒HCID 6344Dichloromethane溶媒

実験手順

To a suspension of selenium dioxide (58 mg) and 2-hydroxybenzoic acid (365 mg) in methylene chloride (10.5 ml) was gradually added an aqueous solution of 80% t-butyl hydroperoxide (11.6 ml) with stirring on a water bath. After 30 minutes, 2-(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-tetradecatetraenenitrile (7.56 g, 26.8 mmol)was added to the mixture, which was then allowed to stand at room temperature for 30 hours. Most of the solvent was removed by evaporation in vacuo, and the residue was dissolved in ether. The organic layer was washed with saturated aqueous sodium bicarbonate, dried over MgSO4, and concentrated. The resultant residue was subjected to silica gel column chromatography to give the aimed 4-hydroxy-2-(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-tetradecatetraenenitrile (2.53 g, 31%). The starting material was also recovered (3.10 g, 40%) in the column chromatography. The yield of the aimed product based on the consumed starting material was 52%.

後処理

  1. waitto stand at room temperature for 30 hours
  2. customMost of the solvent was removed by evaporation in vacuo
  3. dissolutionthe residue was dissolved in ether
  4. washThe organic layer was washed with saturated aqueous sodium bicarbonate
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-8cb5b0b5c50143bfa4c124459d8c89ed
出典データセット
uspto-grants-1994_04
特許番号
US05304661

関連ノート

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