3-acetylcoumarin
Synthesis of 3-Acetylcoumarin
Introduction
In thi lab we were asked to make coumarin. Coumarin is a fragrent organic chemical compound. It is a natural substance found in many plants. The name comes from the french term for tonka bean. The substance was first isolated as a natural product in 1820. Coumarin has been showed to be useful in biological activity, but they have been approved for few pharmacutical uses. It has been reported that coumarin activity includes HIV, tumors, hypertension,arrhythmia, osteoporosis, inflammation, sepsis, asthma and analgesic.
There are various approche to the synthesis of coumarin. They are perkin reaction, knovenagel condensation, clasen rearragenment and pechmann condensation. The synthesis that’s important to us is the knovenagel condensation (Figure 1) and the perkin reaction (Figure 2). The knovenagel condensation is named after Emil Knovenagel. The Knovenagel condensation is a key to the commercial production of the antimalarial drug lumafrantrine. The perkin reaction was develop by William Henry Perkin. This reaction is useful to make cinnamic acid.
Experimental Section
This experiment was performened on a 40 mmol scale. The materials we will use will be salicylaldehyde, Ethyl acetoacetane, Piperidine and Ethanol. In a 150ml single-neck round bottom flask equipped with a stir bar, add salicylaldehyde. We used 4.89g or one equivalent. Then add ethyl acetate to the round bottom flask. We added 5.47g or 1.05 equivalent. Add 40 mL of ethanol to the round bottom flask make sure to stir.
While stirring add the piperidine. The amount needed is .107g or .05 equivalent. Equip the round bottom flax to the flux condenser. Place the round bottom flax on a hot plate, oil bath or in any appropriate size heatin mantle. Bring the reaction mixture to reflux for 30 to 40 minutes. The reaction mixture will change from a yellow red to a dark orange.
The after the feflux had finished remove the heat
Introduction
In thi lab we were asked to make coumarin. Coumarin is a fragrent organic chemical compound. It is a natural substance found in many plants. The name comes from the french term for tonka bean. The substance was first isolated as a natural product in 1820. Coumarin has been showed to be useful in biological activity, but they have been approved for few pharmacutical uses. It has been reported that coumarin activity includes HIV, tumors, hypertension,arrhythmia, osteoporosis, inflammation, sepsis, asthma and analgesic.
There are various approche to the synthesis of coumarin. They are perkin reaction, knovenagel condensation, clasen rearragenment and pechmann condensation. The synthesis that’s important to us is the knovenagel condensation (Figure 1) and the perkin reaction (Figure 2). The knovenagel condensation is named after Emil Knovenagel. The Knovenagel condensation is a key to the commercial production of the antimalarial drug lumafrantrine. The perkin reaction was develop by William Henry Perkin. This reaction is useful to make cinnamic acid.
Experimental Section
This experiment was performened on a 40 mmol scale. The materials we will use will be salicylaldehyde, Ethyl acetoacetane, Piperidine and Ethanol. In a 150ml single-neck round bottom flask equipped with a stir bar, add salicylaldehyde. We used 4.89g or one equivalent. Then add ethyl acetate to the round bottom flask. We added 5.47g or 1.05 equivalent. Add 40 mL of ethanol to the round bottom flask make sure to stir.
While stirring add the piperidine. The amount needed is .107g or .05 equivalent. Equip the round bottom flax to the flux condenser. Place the round bottom flax on a hot plate, oil bath or in any appropriate size heatin mantle. Bring the reaction mixture to reflux for 30 to 40 minutes. The reaction mixture will change from a yellow red to a dark orange.
The after the feflux had finished remove the heat