Hydrochloric Acid → HCID 54758303, compound

Participants

Reaction Steps

To a solution of commercial 4-propyl-benzaldehyde (5 g) and ethyl acetoacetate (8.77 g) in ethanol (10 ml) piperidine (1 ml) was added with stirring at rt. The yellow solution was kept at rt overnight. The precipitate was collected by suction filtration and washed with ethanol. After drying in vacuo 8.75 g of a faint yellowish solid (the bis-adduct of acetoacetate to the benzaldehyde) was isolated. The finely divided solid was added in portions to 40% NaOH (120 g) with stirring. The resulting yellow slurry was stirred at reflux for 2 h. After cooling in an ice bath the mixture was acidified by portionwise addition of conc. HCl (110 ml) to give a precipitate. The solid was collected by suction filtration and washed with water. After drying in vacuo 3-(4-propylphenyl)glutaric acid (4.89 g) was obtained. The suspension of finely divided 3-(4-propylphenyl)glutaric acid in acetyl chloride (7 ml) was heated to reflux with stirring for 1 h. After cooling to rt precipitation of the product is completed by addition of petrol ether (50 ml). The precipitate is isolated by suction filtration, washed with petrol ether, and recrystallised to give 3-(4-propylphenyl)glutaric anhydride (2.5 g) as colourless crystals.

Provenance & Evidence