- Production Method of 3-Ethoxy-2-cyclohexenone
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3-Ethoxy-2-cyclohexenone (CAS NO.: ), which is also known as Dihydroresorcinol monoethyl ether, could be produced through the following synthetic routes.
In a 2-l. flask fitted with a total-reflux, variable-take-off distillation head is placed a solution of 53 g. (0.472 mole) of dihydroresorcinol, 2.3 g. of p-toluenesulfonic acid monohydrate and 250 ml. of absolute ethanol in 900 ml. of benzene. The mixture is heated to boiling and the azeotrope composed of benzene, alcohol, and water is removed at the rate of 100 ml. per hour. When the temperature of the distilling vapor reaches 78°, the distillation is stopped and the residual solution is washed with four 100-ml. portions of 10% aqueous sodium hydroxide which have been saturated with sodium chloride. The resulting organic solution is washed with successive 50-ml. portions of water until the aqueous washings are neutral and then concentrated under reduced pressure. The residual liquid is distilled under reduced pressure. The yield of 3-ethoxy-2-cyclohexenone, b.p. 66–68.5°/0.4 mm. or 115–121°/11 mm., n29D 1.5015, is 46.6–49.9 g. (70–75%).
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