Реакция #5763

Уравнение реакции

t-butyl hydroperoxide

2-hydroxybenzoic acid

2-(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-tetradecatetraenenitrile

→

4-hydroxy-2-(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-tetradecatetraenenitrile

Растворители

methylene chloride

Условия реакции

Обработка

1. 1
   workup.WAITto stand at room temperature for 30 hours
2. 2
   ДругоеMost of the solvent was removed by evaporation in vacuo
3. 3
   workup.DISSOLUTIONthe residue was dissolved in ether
4. 4
   ПромывкаThe organic layer was washed with saturated aqueous sodium bicarbonate
5. 5
   Сушкаdried over MgSO4
6. 6
   Концентрированиеconcentrated

Методика

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%.

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