Ammonium Chloride → 1-(2-Methoxy-4-methyl-phenyl)-propan-1-ol

Reaction equation

[CH3:1][O:2][C:3]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:4]=1[CH:5]=[O:6].[CH3:12][CH2:13][Mg+].[Br-].[Cl-].[NH4+]>C(OCC)C>[CH3:1][O:2][C:3]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:4]=1[CH:5]([OH:6])[CH2:12][CH3:13]

Participants

Procedure

To a stirring solution of 2-methoxy-4-methylbenzaldehyde (1 g, 6.66 mmol) in diethyl ether (35 ml) at 0° C. is added EtMgBr (2.220 ml, 6.66 mmol). The mixture is stirred for 2 hours and then added to sat ammonium chloride solution. The mixture is extracted with ethyl acetate and the combined organic portions are washed with NaHCO3, water and brine dried (MgSO4) and reducing under vacuum to yield the title product as a clear oil. 1H NMR (400 MHz, CDCl3) δ 7.18 (d, 1H), 6.78 (d, 1H), 6.72 (s, 1H), 4.77 (t, 1H), 3.85 (s, 3H), 2.37 (s, 3H), 1.83 (m, 2H), 0.96 (t, 3H).