Anisole → 1-Acetoxy-2-methyl-3-(4-methoxyphenyl)propene

Participants

Reaction Conditions

Reaction Steps

In an argon gas atmosphere, a four necked flask having a capacity of 200 ml was charged with 19.22 g (100 m moles) of 3,3-diacetoxy-2-methylpropene having a purity degree of 89.6% by mass and 108.14 g (1.0 mole) of anisol. Then, the resultant mixture was mixed with 1.42 g (10 m moles) of boron trifluoride-diethylether complex at an internal temperature of 24° C. for 2 minutes. The mixture was stirred at an internal temperature of 24 to 25° C. for one hour to cause the mixed propene compound and anisol to react with each other. After the reaction was completed, the resultant reaction liquid was washed two times with 20 ml of water and further with 20 ml of saturated aqueous sodium chloride solution. The resultant reaction liquid was subjected to a layer separation treatment, the resultant organic layer was removed by a distillation under reduced pressure (20 mmHg, 55 to 57° C.), the resultant residue was refined by a chromatography on silica gel using an eluting solvent:hexane/ethyl acetate mixture in a mixing volume ratio: 10/1. As a colorless liquid fraction, the target 1-acetoxy-2-methyl-3-(4-methoxyphenyl)propene was obtained in a yield of 93.4% in an amount of 20.58 g.

Provenance & Evidence