ChemicalBook CAS DataBase List Ethyl 4-methoxycinnamate

Ethyl 4-methoxycinnamate synthesis

12synthesis methods

Product Name:Ethyl 4-methoxycinnamate
CAS Number:24393-56-4
Molecular formula:C12H14O3
Molecular Weight:206.24

Ethyl 4-methoxycinnamate synthesis: 4-Methoxycinnamic Acid (0.60 g, 3.36 mmol) was dissolved in 10 mL of dry N,N-dimethylformamide (DMF) in a 25-mL, roundbottomed flask. Cesium carbonate (1.65 g, 5.06 mmol) was added followed by iodoethane (1.0 mL, 12.5 mmol). The flask was capped (rubber septum) and the heterogeneous mixture stirred vigorously at 50 °C for one hour. After this time, HCl (1.0 M, 4.0 mL) was added to quench the reaction. The liquid was decanted from any remaining solid and extracted with 3 : 1 hexanes/ethyl acetate (2 x 10 mL). The organic layer was washed with brine (20 mL), dried with MgSO4, filtered, and solvent removed. The remaining oil solidified on standing to form colorless prisms.

Synthesis of ethyl 4-methoxycinnamate

123-11-5 Synthesis

123-11-5
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$10.00/10g

Ethyl (triphenylphosphoranylidene)acetate

1099-45-2
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$6.00/5g

24393-56-4
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$5.00/250mg

Yield:24393-56-4 77%

Reaction Conditions:

in dichloromethane at 20; for 16 h;Inert atmosphere;

Steps:

(E)-Ethyl 3-(4-methoxyphenyl)acrylate.
To a stirred solution of 4-methoxybenzaldehyde (1.00 mL, 8.25 mmol) in anhydrous dichloromethane (15 mL) under Ar atmosphere was added ethyl (triphenylphosphoranylidene)acetate (3.02 g, 8.66 mmol). The mixture solution was stirred for 16 h at room temperature and then concentrated under reduced pressure. The resulting solid was purified by column chromatography on silica (20% EtOAc/hexanes) to give the desired product as a colorless oil (1.31 g, 6.34 mmol, 77%).

References:

Radomkit, Suttipol;Sarnpitak, Pakornwit;Tummatorn, Jumreang;Batsomboon, Paratchata;Ruchirawat, Somsak;Ploypradith, Poonsakdi [Tetrahedron,2011,vol. 67,# 21,p. 3904 - 3914] Location in patent:supporting information; experimental part

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623-12-1 Synthesis