alpha-Methylcinnamic acid synthesis
- Product Name:alpha-Methylcinnamic acid
- CAS Number:1199-77-5
- Molecular formula:C10H10O2
- Molecular Weight:162.19
100-52-7
123-62-6
1199-77-5
General procedure: Propionic anhydride (300 mmol, 1.6 eq.) was slowly added to a reaction vial containing potassium carbonate (224 mmol, 1.2 eq.) at 0 °C. After stirring for 5 min, benzaldehyde (186 mmol, 1.0 eq.) was added dropwise to the mixture. The reaction mixture was heated to reflux and maintained for 12 hours. Upon completion of the reaction, the mixture was cooled to room temperature using an ice bath, followed by addition of water (appropriate amount) and solid Na2CO3 (30 g) to the reaction mixture. The resulting yellow precipitate was collected by filtration and the filtrate was acidified to pH 6.0 with concentrated HCl to precipitate a solid product of 2-methyl-3-phenylpropenoic acid.
Yield:1199-77-5 62%
Reaction Conditions:
with potassium carbonate at 80;Micellar solution;Heck Reaction;
Steps:
A typical Heck reaction was performed in a double walledglass reactor with reflux condenser at ambient pressure. 153 μL (1.34 mmol) alkene (e.g. styrene) and 158 L (1.50 mmol) arylhalide (e.g. iodobenzene) were dissolved in 46 mL organic sol-vent or aqueous microemulsion in the presence of 0.276 g(2.00 mmol) K2CO3as base and stirred at desired reactiontemperature.1.2-1.4 g of the immobilized catalyst containing15 mg (0.067 mmol) Pd(OAc)2on silica was added to the reactionmixture and the reaction was started. For the Heck reaction withhomogeneous catalyst only 15 mg (0.067 mmol) of palladium (II)acetate was added. The reaction progress was monitored by mea-suring the reactant concentrations at different reaction times byhigh performance liquid chromatography (HPLC).
References:
Volovych;Kasaka;Schwarze;Nairoukh;Blum;Fanun;Avnir;Schom?cker [Journal of Molecular Catalysis A: Chemical,2014,vol. 393,p. 210 - 221]
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