ETHYL 4-PROPIONYLBENZOATE synthesis
- Product Name:ETHYL 4-PROPIONYLBENZOATE
- CAS Number:860344-87-2
- Molecular formula:C12H14O3
- Molecular Weight:206.24
64-17-5
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4219-55-0
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860344-87-2
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Yield:860344-87-2 83%
Reaction Conditions:
with sulfuric acid at 20 - 70; for 22 h;
Steps:
4.1.5.20. 4-(2-(1-(benzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamido)-5-methylthiazol-4-yl)benzoic acid(5f)
General procedure: A mixture of 4-bromopropiophenone (105mg, 0.5mmol) and CuCN (59mg, 0.65mmol) in dry DMF (0.5mL) was refluxed for 10h, then poured into H2O (1,5mL) containing FeCl3 (162mg, 1mmol) and 12N HCl (230μL). The mixture was kept in a water bath at 70°C for 20min and left at room temperature overnight. The solid precipitated was filtered and dissolved in diethyl ether (2ml) and the solution was washed with H2O (2×2ml). The organic layer was dried (MgSO4) and evaporated to obtain 4-propionylbenzonitrile (59mg 74%) with high purity. 4-Propionyl-benzonitrile (46mg, 0.29mmol) was refluxed in EtOH (1ml) and KOH (37mg, 0.64mmol) for 2h to permit the complete hydrolysis of the nitrile. The ethanol solution was evaporated and the residue suspended in water (1ml). The reaction mixture was cooled in ice and adjusted to pH=2 with 12N HCl. The slurry was extracted with ethyl acetate (3×1ml). The combined organic phases were washed with water and saturated sodium chloride, dried over sodium sulfate and evaporated. After lyophilization we obtain 4-propionyl-benzoic acid (44mg, 86%). The foregoing acid (37mg, 0.2mmol) was dissolved in ethanol (1ml) and treated with 97% sulfuric acid (0.1ml). The mixture was stirred at room temperature for 4h, then at T=70°C for 2h and lastly T=40°C for 16h. After evaporation of ethanol, the residue was suspended in water (1ml) and extracted with ethyl acetate (3×1ml). The combined organic phases were washed with water (2×1ml), saturated sodium chloride, dried over sodium sulfate and evaporated. The residue ethyl 4-propionylbenzoate was isolated as colorless oil (34.5mg, 83%).
References:
Liessi, Nara;Cichero, Elena;Pesce, Emanuela;Arkel, Maria;Salis, Annalisa;Tomati, Valeria;Paccagnella, Matteo;Damonte, Gianluca;Tasso, Bruno;Galietta, Luis J.V.;Pedemonte, Nicoletta;Fossa, Paola;Millo, Enrico [European Journal of Medicinal Chemistry,2018,vol. 144,p. 179 - 200]
64-17-5
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153929-32-9
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860344-87-2
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10342-83-3
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860344-87-2
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52129-98-3
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860344-87-2
12 suppliers
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