Ethyl trans-cinnamate

Figure 9.7. The 60-MHz H spectrum of trans-ethyl cinnamate. Sadder Research Laboratories, Division of Bio-Rad Laboratories, Inc. (1966).

Hexanoic acid 2-Phenylethanol trans-Ethyl cinnamate... 

Figure 3b. So - T, absorption in ethyl iodide and phosphorescence (in EPA at 77°K) spectra of trans-ethyl cinnamate. The emission intensity was corrected according to ref. The intensity of emission is relative value. The calculated value only snows the transition energy.

Based upon these principles, iodobenzene was reacted with ethyl acrylate to give trans-ethyl cinnamate (290) in several ionic liquids, including N,N -dialkylimidazolium and JV-alkylpyridinium derivatives with a [Pd(OAc)2] -I-P(C6H5)s catalyst precursor (Scheme 59). In general, the reactions took place at 40-100°C with high yields (in several cases close to quantitative) and the catalyst could be recycled many times without loss of activity. Reaction of benzoic anhydride and butyl acrylate under similar conditions gave trans-butyl cinnamate in 90-95% yields. In this case, the by-product is benzoic acid, which can be reconverted to benzoic anhydride therefore no halide waste is produced. 

To a solution of m-ethyl cinnamate (44, 352 mg, 85% pure, 1.70 mmol) and 4-phenylpyridine-A-oxide (85.5 mg, 29 mol%) in 1,2-dichloromethane (4.0 mL) was added catalyst 12 (38.0 mg, 3.5 mol%). The resulting brown solution was cooled to 4°C and then combined with 4.0 mL (8.9 mmol) of pre-cooled bleach solution. The two-phase mixture was stirred for 12 h at 4°C. The reaction mixture was diluted with methyl-t-butyl ether (40 mL) and the organic phase separated, washed with water (2 x 40 mL), brine (40 mL), and then dried over Na2S04. The drying agent was removed by filtration the mother liquors concentrated under reduce pressure. The resulting residue was purified by flash chromatography (silica gel, pet ether/ether = 87 13 v/v) to afford a fraction enriched in cis-epoxide (45, cis/trans . 96 4, 215 mg) and a fraction enriched in trans-epoxide cis/trans 13 87, 54 mg). The combined yield of pure epoxides was 83%. ee of the cis-epoxide was determined to be 92% and the trans-epoxide to be 65%. 

Baker s yeast catalyzed the regioselective cycloaddition of stable aromatic nitrile oxides ArCNO [Ar = 2,6-C12C6H3, 2,4,6-Me3C6H2, 2,4,6-(MeO)3C6H2] to ethyl cinnamate, ethyl 3-(p-tolyl)acrylate, and tert-butyl cinnamates (218). Reactions of dichloro- and trimethoxybenzonitrile oxides with all three esters proceeded regio- and stereoselectively to form exclusively alkyl tran.v -3,5-diary 1 -... 

Steele, W.V., Chirico, R.D., Cowell, A.B., Knipmeyer, S.E., and Nguyen, A. Thermodynamic properties and ideal-gas enthalpies of formation for trans-methyl cinnamate, a-methyl cinnamaldehyde, methyl methacrylate, l-non3me, trimethylacetic acid, trimethylacetic anhydride, and ethyl trimethyl acetate, J. Chem. Eng. Data, 47(4) 700-714, 2002. 

Ethyl cinnamate, AT50 Ethyl crotonate, AHTT Ethyl 3-cyanoacrylate, AH26 Ethyl trans-3-cyanopropenoate, AH26... 

The Heck reaction between iodobenzene and ethyl acrylate proceeds efficiently using PdCl2 dissolved in 95b, with cholinium acetate as the base and ammonium formate as reducing agent. Trans-QthyX cinnamate is produced in 60% after heating at 80 °C for 1 h. 

Ethylbutyric acid, 216 Ethyl chloroformate, 191, 193 Ethyl cinnamate, cis and trans, 197 Ethyl frans-cinnamate, 171... 

Wittig reactions. Ethylene oxide can be used as the base for generation of Wittig reagents from phosphonium salts. It is often not necessary to prepare the salts thus a mixture of ethylene oxide, triphenylphosphine, and ethyl bromoacetate reacts with benzaldehyde at 25° to give ethyl cinnamate (91% yield, trans.cis = 93 7).3... 

In the presence of Lewis adds, 2-methacrolein, acrolein, E-2-heptenal, acrylic acid, methyl acrylate and ethyl cinnamate are more stable in the s-trans conformation [76, 83, 85, 88] by about 1.5-3.2 kcal mol. The calculated barrier to conformational interconversion is higher (12 kcal mol ). 

Ethyl rrfl/i.s-3-phenylprop-2-enoate trans-Qthyl cinnamate)... 

Methyl 3-phenylpropionate 203-093-8 Methyl cinnamate 203-095-9 Benzyl isobutyrate 203-096-4 Di benzyl 203-098-5 Eccobrite RB Eccobrite RB-6 Stilbene trans-Stilbene Tinopal UNPA-GX 203-104-6 Ethyl cinnamate 203-105-1 Benzyl butyrate 203-106-7 Benzyl isovalerate 203-109-3 Benzyl cinnamate 203-113-5... 

Figure 2 GC/MS chromatograms of fruit juice beverage by (A) DCM extraction and (B) SPME (PDMS) liquid sampling. Peak identification is as follows (1) dichloromethane (2) ethyl butyrate (3) ethyl isovalerate (4) limonene (5) ethyl hexanoate (6) isoamyl butyrate (7) hexanyl acetate (8) cA-3-hexenyl acetate (9) hexanol (10) di -3-hexenol (11) cA-3-hexenyl butyrate (12) furfural (13) benzaldehyde (14) linalool (15) P-terpin-eol (16) butyric acid (17) 2-methyl butyric acid (18) a-terpineol (19) hexanoic acid (20) cw-methyl cinnamate (21)l-(2-furyl)-2-hydroxyethanone (22) furaneol (23) trans-methyl cinnamate (24) y-decalactone (25) dodecanoic acid (26) (hydroxymethyl)fur-fural.

The couplings of vicinal protons in 1,2-disubstituted alkenes lie in the range 6-12 Hz for cis protons (dihedral angle 0°) and 12-17 Hz for trans protons (dihedral angle 180°), thus also following the Karplus-Conroy equation. Typical examples are the alkene proton AB systems of coumarin (16a, cis) and tra 5-cinnamic acid (16b), and of the cis-trans isomers 17a and b of ethyl isopente-nyl ether, in addition to those in problems 3, 4, 8, 11, 13 and 38. 

The Heck reaction is a C-C coupling reaction where an unsaturated hydrocarbon or arene halide/triflate/sulfonate reacts with an alkene in presence of a base and Pd(0) catalyst so as to form a substituted alkene. Kaufmann et al. showed that the Heck reaction carried out in presence of ILs such as tetra-alkyl ammonium and phosphonium salts without the phosphine ligands, resulted in high yields of product. They attributed the activity to the stabilizing effect of ammonium and phosphonium salts on Pd(0) species. Carmichael et al. used ionic liquids containing either A,A -dialkylimidazolium and A-alkylpyridinium cations with anions such as halide, hexafluorophosphate or tetrafiuoroborate to carry out reactions of aryl halide and benzoic anhydride with ethyl and butyl acrylates in presence of Pd catalyst. An example of iodobenzene reacting with ethyl acrylate to give trans-et vy cinnamate is shown in Scheme 14. 

Fluorination.1 The reagent reacts with Irani- and cu-stilbene, preferentially by s> -addilion. Only the sr/i-adducts are isolable in the reaction of 1 with ethyl trans-anti e -cinnamate (equation I). OAc... 

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