Sodium Hydroxide → 1-(Diethoxymethyl)cyclopropane-1-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

In toluene (260 ml) was dissolved 1,1-cyclopropane dicarboaldehyde (30 g, 306 mmol). The resulting solution was stirred at 20° C. To the reaction mixture was added dropwise a solution of p-toluenesulfonate monohydrate (153 mg, 0.77 mml) in toluene (10 ml) and the mixture was cooled to the internal temperature of 5° C. or less. A solution of ethyl orthoformate (49.7 g, 335 mmol) in toluene (30 ml) was gradually added dropwise. After completion of the dropwise addition, the mixture was stirred continuously for 1 hour over an ice bath. At the internal temperature elevated to 25° C., stirring was conducted for further 1 hour. After completion of the reaction was confirmed, the internal temperature was adjusted to 15° C., at which 2 mol/l-NaOH (3.75 ml) was added, followed by stirring for 1 hour. Water (50 ml) was added and the mixture was separated and extracted. Toluene was then evaporated under reduced pressure, whereby a colorless oil (55.8 g, stoichiometric) was obtained. Concerning a ratio of the monoacetal compound and the diacetal compound, that of the monoacetal compound was found to be 95% or greater. The instrumental analysis data were similar to those described in Example 1.

Provenance & Evidence