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ChemicalBook CAS DataBase List Cinnamic acid
621-82-9

Cinnamic acid synthesis

13synthesis methods
Two isomers, trans- and cis- exist; the trans-isomer is of interest for use in flavoring; in addition to the extraction from natural sources (storax), it can be prepared as follows: (1) from benzaldehyde, anhydrous sodium acetate and acetic anhydride in the presence of pyridine (Perkin reaction); (2) from benzaldehyde and ethyl acetate (Claisen condensation); (3) from benzaldehyde and acetylene chloride; (4) by oxidation of benzylidene acetone with sodium hypochlorite.
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Yield:621-82-9 98%

Reaction Conditions:

Stage #1: acrylic acidwith potassium tert-butylate in water at 20; for 0.166667 h;Inert atmosphere;
Stage #2: bromobenzenewith C16H21Br2N3Pd in water at 120; for 24 h;Inert atmosphere;Sealed tube;Mizoroki-Heck reaction;

Steps:

4.2.1. General procedure for the NHC-Pd(II) complex 1-catalyzed Mizoroki-Heck reaction

General procedure: (If olefin is acrylic acid) Under N2 atmosphere, acrylic acid 3a (1.5 mmol), KOtBu (3.0 equiv) and H2O (2.0 mL) were added into a seal tube and the mixture was stirred at room temperature for 10 min. Then NHC-Pd(II) complex 1 (1.0 mol %) and aryl halides 2 (1.0 mmol) were added. The mixture was stirred vigorously at 120 °C (for bromides) or 100 °C (for iodides) for 24 h. After cooling to room temperature, HCl (4 M) was dropped into the reaction mixture to reach a pH of 1, extracted with EtOAc, washed with brine, dried over anhydrous Na2SO4. The solvent was removed under reduced pressure and the residue was purified by a flash column chromatography (SiO2) to give the pure product.

References:

Tang, Yi-Qiang;Chu, Chun-Yan;Zhu, Lei;Qian, Bin;Shao, Li-Xiong [Tetrahedron,2011,vol. 67,# 49,p. 9479 - 9483] Location in patent:experimental part

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