Veratrole → 1-Acetoxy-2-methyl-3-(3,4-dimethoxyphenyl)propene

Participants

Reaction Conditions

Reaction Steps

In an argon gas atmosphere, a four necked flask having a capacity of 100 ml was charged with 69.2 g (500 m moles) of 1,2-dimethoxybenzene and 9.61 g (50 m moles) of 3,3-diacetoxy-2-methylpropene having a purity degree of 89.6% by mass. Then, the resultant mixture was mixed with 1.36 g (10 m moles) of zinc chloride at an internal temperature of 25 to 26° C. The mixture was stirred at an internal temperature of 25 to 26° C. for 1.5 hours to cause the mixed compounds to react with each other. After the reaction was completed, the resultant reaction liquid was washed three times with 50 ml of saturated aqueous sodium chloride solution. The resultant reaction liquid was subjected to a layer separation treatment, the resultant organic layer was collected and subjected to a distillation under reduced pressure (8 to 10 mmHg, 80 to 84° C.), the resultant residue was refined by a chromatography on silica gel using an elusion solvent:hexane/ethyl acetate mixture in a mixing ratio by volume of 10/1. The target 1-acetoxy-2-methyl-3-(3,4-dimethoxyphenyl)propene was obtained in a yield of 95.1% in an amount of 11.9 g in the form of a colorless liquid.

Provenance & Evidence