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

HRID 1464469

Reaktionsgleichung

Reaktionsgleichung von HRID 1464469
[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]

Komponenten

6

Edukt 3

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

Produkt 1

HCID 867472134-Hydroxy-2-(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-tetradecatetraenenitrileAusbeute 317,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24007Selenium DioxideKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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%.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-8cb5b0b5c50143bfa4c124459d8c89ed
Quelldatensatz
uspto-grants-1994_04
Patentnummer
US05304661

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