p-Toluenesulfonic acid → 6-Bromo-2,2,4,4-tetramethylchroman
Reaktionsgleichung
[Br:1][C:2]1[CH:7]=[CH:6][C:5](O)=[C:4]([C:9]([CH3:16])([CH3:15])[CH2:10][C:11]([OH:14])([CH3:13])[CH3:12])[CH:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:6][CH:7]=1)[O:14][C:11]([CH3:13])([CH3:12])[CH2:10][C:9]2([CH3:16])[CH3:15]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
A solution of 4-bromo-2-(3-hydroxy-1,1,3-trimethyl-butyl)-phenol (1.1 g, 3.92 mmol) and p-toluene sulfonic acid (0.744 g, 3.92 mmol) in benzene (20 mL) was refluxed overnight. The reaction mixture cooled to ambient temperature, filtered on silica gel and washed with 10% ethyl acetate in hexane. The filtrate and washings were evaporated in vacuo to an oil which was subjected to flash column chromatography over silica gel (230-400 mesh) using 5% ethyl acetate in hexane as the eluent to afford the title compound as a pale yellow oil (0.84 g, 80%).