Dichloromethane → 2-Propenoic acid, 2-methyl-, tetrahydro-5-oxo-3-furanyl ester

Participants

Reaction Conditions

Reaction Steps

In a glass flask equipped with a stirrer, two dropping funnels, a thermometer and a Dimroth condenser, β-hydroxy-γ-butyrolactone (91.1 g, 0.875 mol) having a purity of 98% obtained by repeating the process of Example 1 and 500 ml of dry dichloromethane were charged, and then triethylamine (117.5 g, 1.16 mol) was charged in one dropping funnel and methacrylic acid chloride (112 g, 1.071 mol) was charged in another dropping funnel. The atmosphere in the glass flask was replaced by nitrogen and then cooled to −60 to −70° C. in a dry ice-acetone bath. While stirring in the glass flask, triethylamine and methacrylic acid chloride were added dropwise with adjusting so that the amount of triethylamine becomes small excess to that of methacrylic acid chloride. After the completion of the dropwise addition, stirring was continued for 3 hours. To the reaction solution, 300 ml of water was added and a small amount of Celite was added, followed by filtration. The filtrate was washed three times with 300 ml of water using a separatory funnel and dried by adding 80 g of magnesium sulfate and, after filtering, the filtrate was concentrated to obtain 175 g of crude β-methacryloyloxy-γ-butyrolactone. This β-methacryloyloxy-γ-butyrolactone was purified by silica gel column chromatography to obtain β-methacryloyloxy-γ-butyrolactone (106.3 g, 0.625 mol).

Provenance & Evidence