ChemicalBook CAS DataBase List Ethyl 3-oxo-4-phenylbutanoate

Ethyl 3-oxo-4-phenylbutanoate synthesis

10synthesis methods

Product Name:Ethyl 3-oxo-4-phenylbutanoate
CAS Number:718-08-1
Molecular formula:C12H14O3
Molecular Weight:206.24

The synthesis of Ethyl 3-oxo-4-phenylbutanoate is as follows:Monoethyl monopotassium malonate (12.9 g, 2.3 equivalents) was mixed with tetrahydrofuran (200 ml), and the mixture was cooled to 5°C. Triethylamine (8.2 g, 2.5 equivalents) and magnesium chloride (8.62 g, 2.8 equivalents) were added, and the mixture was stirred at 5 to 20°C for 3 hours. The reaction mixture was cooled to 5°C. Phenacyl chloride (5 g, 32 mmol, 1 equivalent) was gradually added, and the mixture was stirred at 5 to 20°C for 63 hours. The mixture was cooled to 5°C, and 1 N hydrochloric acid (30 ml) was added. Tetrahydrofuran was evaporated away under reduced pressure, and extraction was carried out with ethyl acetate (50 ml). The organic layer was washed with 1 N hydrochloric acid (30 ml), water (10 ml), saturated aqueous solution of sodium hydrogencarbonate (30 ml) and water (10 ml) in order. The solvent was evaporated away under reduced pressure to obtain the Ethyl 3-oxo-4-phenylbutanoate as a pale yellow oil (5.82 g, yield: 86 %).

2033-24-1 Synthesis

2033-24-1
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$6.00/25g

64-17-5 Synthesis

64-17-5
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$10.00/50g

103-80-0
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$13.00/25g

718-08-1
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$100.83/1g

Yield:718-08-1 98.8%

Reaction Conditions:

Stage #1: 2,2-dimethyl-1,3-dioxane-4,6-dione;3?phenylpropanoyl chloridewith pyridine in dichloromethane at 0 - 20;Inert atmosphere;
Stage #2: ethanol for 2.5 h;Inert atmosphere;Reflux;

Steps:

(2) Synthesis of 1t

To the solution of 2,2-dimethyl-1,3-dioxane-4,6-dione (Meldrum’s Acid) (23.75 g, 0.165 mol) and anhydrous pyridine (32.5 mL, 0.4 mol) in CH2Cl2 (100 mL), phenylacetyl chloride (25.50 g, 0.165 mol) was added dropwise under 0 °C. The mixture was stirred at 0 °C for 1 hour and raised to room temperature for another 1 hour. One hundred milliliter 2N aq HCl was added to stop the reaction. The organic phase was separated and the aqueous layer extracted with CH2Cl2. The organic layer was collected, evaporated the solvent to give light yellow solid. After washing by little amount of EtOH, white crystal was obtained and directly refluxed with anhydrous EtOH (250 mL) for 2.5 hours. After concentration under reduced pressure, light yellow oil was obtained which can be used in the next step without purification. Purification by column chromatography with EtOAc-petroleum ether (1:80) yields compound 2 as colorless oil (33.05 g, 98.8%).

References:

Wang, Yiqiong;Zhang, Lingyu;Zhang, Songlin [Synthesis,2022,vol. 54,# 24,p. 5491 - 5499]

6148-64-7 Synthesis