1-(2-Hydroxy-5-methoxyphenyl)ethan-1-one → 2-(2-Hydroxypropan-2-YL)-4-methoxyphenol
Reaktionsgleichung
[CH3:1][Mg]Br.[OH:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:6]=1[C:13](=[O:15])[CH3:14]>C1COCC1>[OH:15][C:13]([C:6]1[CH:7]=[C:8]([O:11][CH3:12])[CH:9]=[CH:10][C:5]=1[OH:4])([CH3:1])[CH3:14]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To a solution of methylmagnesium bromide (221 ml, 665 mmol) in 800 ml THF at 0° C. was added 1-(2-hydroxy-5-methoxy-phenyl)-ethanone (20.21 g, 302 mmol) in portions over 30 min. The mixture was allowed to warm to room temperature. After 16 h the mixture was quenched by the slow addition of 10% NH4Cl, carefully acidified to pH=1 (slow addition) with concentrated HCl and extracted with Et2O. The combined organics were washed with H2O, washed with brine, died over MgSO4, filtered and concentrated in vacuo to give 2-(1-hydroxy-1-methyl-ethyl)-4-methoxy-phenol (50.57 g, 100%) as a tan solid.