2-Propenoic acid, 3-[4-(4-morpholinyl)phenyl]- synthesis
- Product Name:2-Propenoic acid, 3-[4-(4-morpholinyl)phenyl]-
- CAS Number:66377-37-5
- Molecular formula:C13H15NO3
- Molecular Weight:233.2631
Yield:66377-37-5 75%
Reaction Conditions:
with piperidine;pyridine at 80 - 115; for 4 h;
Steps:
4 General method for preparation of (E)-3-(4-substituted phenyl)acrylic acid
General procedure: A mixture of 0.208 g. (0.002 mol) of malonic acid and 0.166 g.(0.001 mol) of 4-substituted benzaldehyde Ia-g and (5 mL) of pyridinewas prepared. Malonic acid is dissolved by shaking andwarming on a steam bath. Catalytic amount of piperidine was thenadded and the mixture was heated at 80-85 C for 1 h. After whichthe mixture was heated under reflux (109-115 C) for an additional3 h. The reaction mixture was then cooled and poured intocold water. The mixture was then acidified by slow addition of concentratedhydrochloric acid with stirring. The formed light crystalswere separated by filtration and washed 4 times with cold water.The crude acid was dissolved in a solution of 5% sodium hydroxide.The resulting solution was filtered, diluted with an additionalwater, and acidified by adding concentrated hydrochloric acid.The formed solid was filtered and washed with cold water. Thesolid was further purified by using methanol as the solvent of crystallizationto yield titled compounds IIIa-g.(E)-3-(4-Morpholinophenyl) acrylic acid IIId (E)
Yield 75% as orange solid, mp 198 °C, (as reported)
[57]
.
References:
Abdel-Atty, Mona M.;Farag, Nahla A.;Kassab, Shaymaa E.;Serya, Rabah A.T.;Abouzid, Khaled A.M. [Bioorganic Chemistry,2014,vol. 57,p. 65 - 82]
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