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ChemicalBook CAS DataBase List Ethyl benzoate
93-89-0

Ethyl benzoate synthesis

14synthesis methods
By esterification of ethyl alcohol and benzoic acid in the presence of anhydrous aluminum sulfate and a trace of sulfuric acid; by transesterification of methyl benzoate with ethanol in the presence of potassium ethylate
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Yield:64511-21-3 99% ,93-89-0 94%

Reaction Conditions:

Stage #1: ethyl Pentafluoropropionatewith sodium hydride in tetrahydrofuran at 20; for 0.166667 h;Inert atmosphere;Schlenk technique;
Stage #2: dihydrochalcone in tetrahydrofuran at 0; for 3 h;Inert atmosphere;Schlenk technique;Reflux;
Stage #3: with hydrogenchloride in tetrahydrofuran;water at 0; for 0.25 h;Inert atmosphere;Schlenk technique;

Steps:

General procedure for ‘trifluoroacetic ester/ketone metathesis’ and the preparation of TFMKs

General procedure: Under Ar atmosphere in a dry Schlenk tube, a mixture of NaH (6.0 mmol) and trifluoroacetate (6.0 mmol) was stirred in THF (5 mL) at room temperature for 10 min. To this mixture enolizable ketones (5.0 mmol) in THF (5 mL) was added dropwise at 0 °C under Ar atmosphere. After stirring for 2-6 h at reaction temperature, the reaction solution was cooled to 0 °C again and quenched with 6 mL of 1 mol/L HCl. After stirring for additional 15 min, the mixture was neutralized with saturated NaHCO3 solution. After usual workup, the residue was purified by chromatography on silica gel to afford the trifluoromethyl alkyl ketone products.

References:

Zhou, Yuhan;Yang, Dongmei;Luo, Gen;Zhao, Yilong;Luo, Yi;Xue, Na;Qu, Jingping [Tetrahedron,2014,vol. 70,# 31,p. 4668 - 4674]

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