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ChemicalBook CAS DataBase List Propanoicacid,2-formyl-3-oxo-,ethylester

Propanoicacid,2-formyl-3-oxo-,ethylester synthesis

4synthesis methods
-

Yield:80370-42-9 100%

Reaction Conditions:

with sodium hydride in diethyl ether at 0 - 20; for 15 h;

Steps:

28 Production of (ethoxycarbonyl)malondialdehyde
12.6 g of sodium hydride (purity: 60%, 525.0 mmoles) was washed with diethyl ether by decantation several times and then made into a solution in 500 ml of diethyl ether. Thereto were added, in a nitrogen current at 0 to 10°C, 194 g (2.6 moles) of ethyl formate and 50 g (262.0 mmoles) of ethyl 3,3-diethoxy-propionate. The resulting mixture was stirred at room temperature for 15 hours to give rise to a reaction. After confirmation of the completion of the reaction, the reaction mixture was poured into water, followed by washing with diethyl ether. The resulting aqueous layer was allowed to have a pH of 1 with hydrochloric acid, followed by extraction with dichloromethane. The resulting organic layer was washed with an aqueous sodium chloride solution and then dried over anhydrous magnesium sulfate. The resulting solution was subjected to vacuum distillation to remove the solvent contained therein, to obtain 37.6 g (yield: 100%) of crude (ethoxycarbonyl)malondialdehyde as a dark red oily substance. 1H-NMR [CDCl3/TMS, δ (ppm)]: 9.09 (2H,s), 5.26 (1H,s), 4.27 (2H,q), 1.28 (3H,t)

References:

KUMIAI CHEMICAL INDUSTRY CO., LTD.;IHARA CHEMICAL INDUSTRY CO., LTD. EP1364946, 2003, A1 Location in patent:Page/Page column 196

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