Methanol → 3,3-dimethoxypentane

Participants

Reaction Conditions

Reaction Steps

First, 43.11 g (50.1 mmol) of 3-pentanone, 43.11 g (1.35 mol) of methanol, and 0.43 g (2.26 mmol) of p-toluenesulfonic acid monohydrate were added to a 3-necked flask (300 ml volume) equipped with a thermometer, a mechanical stirrer and a dropping funnel, and cooled to 5° C. Next, 63.03 g (525 mmol) of trimethyl orthoacetate was added dropwise to this solution over a period of 90 minutes while keeping internal temperature at 10° C. or lower. Then the temperature of the reaction mixture was raised to room temperature and the reaction mixture was agitated for 2 hours. The reaction solution was neutralized with 1.0 g (4.63 mmol) of 25% sodium methoxide/methanol solution, and then distilled under reduced pressure to give 59.34 g of 3,3-dimethoxypentane (boiling point: 55-57° C./50 torr, yield of approximately 100%).

Provenance & Evidence