1-Methoxy-2-propanol → 2',6'-Dimethyl-N-(2-Methoxy-1-Methylethoxymethyl) 2-Chloroacetanilide
Reaction equation
[CH3:1][C:2]1[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[C:3]=1[N:4]([CH2:9]Cl)[C:5](=[O:8])[CH2:6][Cl:7].[CH3:16][O:17][CH2:18][CH:19]([CH3:21])[OH:20]>C(Cl)CCl>[CH3:1][C:2]1[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[C:3]=1[N:4]([CH2:9][O:20][CH:19]([CH3:21])[CH2:18][O:17][CH3:16])[C:5](=[O:8])[CH2:6][Cl:7]Participants
4
Procedure
About 12.3 g (0.050 mole) of 2',6'-dimethyl-N-(chloromethyl) 2-chloroacetanilide dissolved in twenty (20) ml of ethylene dichloride was added to 22.5 g (0.25 mole) of 2-methoxy-1-methyl ethanol. The solution was allowed to stand one hour at room temperature. Excess alcohol and HCl was removed under vacuum on a rotary evaporator. The residual oil was treated with an additional 22.5 g fresh alcohol for 30 minutes at 60° C. Excess alcohol and HCl was removed as before at 65° C./1 mm Hg. The light yellow oily residue weighed 14.86 g (99.1% yield). Refractive index of the oil, n26D 1.5263. Proton NMR was consistent with structure.