tert-Butanol → Phenol, 2-(1,1-dimethylethyl)-4-(1,1,3,3-tetramethylbutyl)-

反応式

[C:1]([C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)([CH2:4][C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:3])[CH3:2].[C:16](O)([CH3:19])([CH3:18])[CH3:17]>C(O)(C(F)(F)F)=O.O>[C:16]([C:13]1[CH:14]=[C:9]([C:1]([CH2:4][C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:2])[CH3:3])[CH:10]=[CH:11][C:12]=1[OH:15])([CH3:19])([CH3:18])[CH3:17]

参加物

実験手順

4-t-octylphenol (160 g, 0.78 mole) was dissolved in 400 ml anhydrous TFA. T-butyl alcohol (94.3 g, 1.27 mole) was added with stirring. The mixture was stoppered and stirred for 24 hours at ambient (~22° C.) temperature. This solution was diluted with 600 ml water, and the resulting upper organic layer was isolated in a separatory funnel. The crude product, 2-t-butyl-4-t-octylphenol, was dried over anhydrous magnesium sulfate and purified by eluting 35 g of the mixture with 70:30 hexanes:dichloromethane (v/v) in a 5×20 cm silica column, then eluted with 300 to 700 ml of solvent and collected in aliquots of 50 ml. Aliquots showing a single spot by TLC on silica eluted with 70:30 hexanes:dichloromethane (v/v) were combined and rotoevaporated to a thick syrup for a yield of 54%.