Salicylic Acid → 14-Hydroxy-2-(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-tetradecatetraenenitrile

HRID 1110175

반응식

HRID 1110175 반응식
[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][CH2:34][C:33]([CH3:35])=[CH:32][CH2:31][CH2:30][C:29]([CH3:36])=[CH:28][CH2:27][CH2:26][C:25]([CH3:37])=[CH:24][CH:23]=[C:20]([CH:18]([CH3:17])[CH3:19])[C:21]#[N:22]

참가 물질

6

반응물 3

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

생성물 1

HCID 5434830814-Hydroxy-2-(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-tetradecatetraenenitrile수율 317.6%

시약·촉매·용매 2

HCID 24007Selenium Dioxide촉매HCID 6344Dichloromethane용매

실험 절차

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 14-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 as 52%.

후처리

  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

출처 및 근거

ORD 기록
ord-229e6ebae67c49df94db2de2aa9ed455
출처 데이터셋
uspto-grants-1994_06
특허 번호
US05324869

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