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Methyl 4-methylcinnamate

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Methyl 4-methylcinnamate Basic information
Preparation Uses Application
Product Name:Methyl 4-methylcinnamate
Synonyms:(E)-3-p-Tolyl-acrylicacidmethylester;4-methyl cinnamic acid meth;4-methyl-trans-cinnamicacidmethylester;E-3-p-Tolyl-acrylicacidmethylester;4-Methylcinnamic acid methyl ester;Methyl (2E)-3-(4-methylphenyl)propenoate;Methyl (E)-p-methylcinnamate;trans-3-(p-Tolyl)-2-propenoic acid methyl ester
CAS:20754-20-5
MF:C11H12O2
MW:176.21
EINECS:
Product Categories:Aromatic Cinnamic Acids, Esters and Derivatives
Mol File:20754-20-5.mol
Methyl 4-methylcinnamate Structure
Methyl 4-methylcinnamate Chemical Properties
Melting point 60-61℃
Boiling point 273℃
density 1.057
Fp 152℃
storage temp. Sealed in dry,Room Temperature
AppearanceWhite to off-white Solid
InChIInChI=1S/C11H12O2/c1-9-3-5-10(6-4-9)7-8-11(12)13-2/h3-8H,1-2H3/b8-7+
InChIKeyWLJBRXRCJNSDHT-BQYQJAHWSA-N
SMILESC(OC)(=O)/C=C/C1=CC=C(C)C=C1
Safety Information
Hazard Codes Xi
MSDS Information
Methyl 4-methylcinnamate Usage And Synthesis
Preparation

Using polyethylene glycol (PEG) as a phase transfer catalyst and PdCl2 as the catalyst in a solid-liquid phase, METHYL 4-METHYLCINNAMATE was synthesized in a yield of 73.1%. This reaction exhibits high selectivity and the product is easily separated, making it another good method for the synthesis of METHYL 4-METHYLCINNAMATE.
In a 100 mL four-necked flask equipped with a reflux condenser, thermometer, and dropping funnel, PdCl2 (0.15 mmol), NaHCO3 (37.5 mmol), PEG-800 (5 mmol), and DMF (10 mL) were added. The mixture was heated to 70 °C under nitrogen protection, then cooled to room temperature. Iodobenzene (15 mmol) and methyl methacrylate (30 mmol) were then added through a dropping funnel, and the mixture was heated to 120 °C for 6 h. After filtration, the reaction solution was extracted with water and then with diethyl ether. The solvent in the extract was removed by rotary evaporation. GC analysis showed a yield of 73.1%.

The pure product was obtained by column chromatography (petroleum ether: ethyl acetate = 10:1), and determined by IR, 1H NMR and GC-MS.
UsesMethyl p-methylcinnamate is a pharmaceutical intermediate used in the synthesis of the antithrombotic drug ozagrel sodium.
ApplicationMethyl methyl cinnamate has a high ultraviolet light absorption rate and can effectively resist ultraviolet rays in the range of 280~320nm. It is widely used in sunscreen cosmetics, textiles, polymers and pharmaceutical intermediates.
Synthesis Reference(s)Synthetic Communications, 17, p. 1839, 1987 DOI: 10.1080/00397918708077329
Tag:Methyl 4-methylcinnamate(20754-20-5) Related Product Information
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