Acetic Acid → 3-Formylbut-2-enyl acetate

Participants

Reaction Conditions

Reaction Steps

4-Acetoxy-2-methyl-1-chloro-2-butene (7.8 g) was added to a suspension of hexamethylenetetramine (6.7 g) in acetonitrile (47 ml), and the mixture was stirred at room temperature for 16 hours. The resulting crystals were separated by filtration to give crystals (12.5 g) of the quaternary ammonium salt. The salt (7.9 g) was dissolved in water (50 ml), and toluene (100 ml) was added. Acetic acid (1.5 g per addition) was added 30 minutes, 1 hour and 2 hours after the beginning of the reaction with stirring at 75° C. The reaction was stopped 6 hours after the beginning of the reaction. The toluene layer was separated and concentrated. The remaining oil was purified by silica gel column chromatography to give 4-acetoxy-2-methyl-2-buten-1-al (2.6 g, 74%).

Provenance & Evidence