4-Methylanisole → Ethyl 4-(2-methoxy-5-methylphenyl)-4-oxobutanoate

Participants

Reaction Steps

A solution of p-methylanisole (100 g, 0.81 mole), β-carbethoxypropionylchloride (96%, 230 g, 1.22 mole), and CH2Cl2 (800 mL) was stirred under N2 at 0° as AlCl3 (131 g, 0.94 mole) was added over 2 hours. The reaction mixture was stirred at room temperature for 20 hours, then was poured onto ice and the layers were separated. The aqueous layer was extracted with CH2Cl2. The combined organic layers were washed with water, saturated aqueous NaHCO3, 1N KOH, H2O, saturated aqueous NaCl, dried (MgSO4), filtered, and evaporated (in-vacuo) to obtain a yellow oil.

Provenance & Evidence