반응 #5763

반응 방정식

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

용매

methylene chloride

반응 조건

후처리

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

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 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%.

출처