6-chloro-2-oxo-2H-chromene-3-carbonyl chloride synthesis
- Product Name:6-chloro-2-oxo-2H-chromene-3-carbonyl chloride
- CAS Number:72973-49-0
- Molecular formula:C10H4Cl2O3
- Molecular Weight:243.04
883-92-1
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Yield:-
Reaction Conditions:
with thionyl chloride for 2 h;Reflux;
Steps:
2.4. The general procedures for the synthesis of substituted coumarin-3-carboxylic acid ester compounds
General procedure: The substituted coumarin-3-carboxylic acid ethyl esters (Scheme 2) were prepared by Knoevenagel reaction. To a mixture of diethyl malonate (1 mmol) and the appropriate salicylaldehyde (1 mmol) in ethanol (10 ml) was added piperidine (5 mol %) and the reaction mixture was stirred at the room temperature. The progress of the reaction was monitored by TLC. After completion of the reaction, the solvent was removed under vacuum and the residue was purified by chromatography. The obtained substituted coumarin-3-carboxylic acid ethyl ester (2 mmol) was dissolved in 10% NaOH (50 ml), then 3 N HCl (50 ml) was added the mixture. The suspension was filtered and dried under vacuum to provide substituted coumarin-3-carboxylic acid. The coumarin-3-carboxylic acid (2 mmol) was added to thionyl chloride (30 ml), the reaction mixture was refluxed for about 2 h, the thionyl chloride was removed under vacuum. The desired substituted coumarin-3-carbonyl chloride was obtained. To a mixture of substituted coumarin-3-carbonyl chloride (2 mmol) and toluene (20 ml) or ethyl ether (20 ml) was added dropwise appropriate alcohol (2 mmol) and then the reaction mixture was refluxed for about 12 h. The solvent was removed under vacuum and the residue was purified by chromatography.
References:
Liu, Jinbing;Wu, Fengyan;Chen, Lingjuan;Zhao, Liangzhong;Zhao, Zibing;Wang, Min;Lei, Sulan [Food Chemistry,2012,vol. 135,# 4,p. 2872 - 2878]
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