Cinnamic acid ethyl ester

Cinnamic acid ethyl ester Fr fixed oil° ° Cinnamic acid Fr fixed oil° ... 

T. B. Otero. Identification of cinnamic acid ethyl ester and 4-vinylphenol in off-flavour olive oils. Ann Chim Acta 1991 247(2) 295-297. 

Ethyl cinnamate Cinnamic acid, ethyl ester (8) 2-Propenoic acid, 3-phenyl-, ethyl ester (9) (103-36-6)... 

Cinnamic acid ethyl ester is a carbonyl compound, which like ben/.ophenone has the ability to accept an electron to form a rather stable anion radical. As tin t. /hunsaturated ester it may produce 1.2- and... 

Methyl, ethyl, n-propyl, isopropyl, n-hutyl, benzyl, cyclohexyl esters of formic, acetic, oxalic, succinic, tartaric, citric, benzoic, salicylic (and other substituted benzoic acids), phthalic and cinnamic acids phenyl esters of acetic, benzoic and salicylic acids. 

The anionic tenside chiral diphosphine 8 was used to generate rhodium catalysts for the hydrogenation of the prochiral olefm (Z)-2-(N-acetamido)cinnamic acid methyl ester in micellar ethyl acetate/H20 two-phase systems [42], The yield (100%) and enantiomeric excess (69%) were considerably higher than those observed with the tetrasulfonated bis(diphenylphosphino)pentane (32% yield and 20% ee) and the reaction time was shorter (1.5 versus 20 h) [42]. 

Ethyl diisopropylcinnamate CAS 32580-72-6 EINECS/ELINCS 251-109-7 Synonyms Cinnamic acid, 2,4-diisopropyl-, ethyl ester 2,4-Diisopropylcinnamic acid, ethyl ester... 

Phenyl-2-propenoic acid, ethyl ester. See Ethyl cinnamate,... 

Cinnamic acid can be readily esterified by the Fischer-Speier method without any risk of the addition of hydrogen chloride at the double bond. Proceed precisely as for the preparation of ethyl benzoate (p. 104), using 20 g. of cinnamic acid and 20 ml. of rectified spirit. When the crude product is poured into water, a sharp separation of the ester is not readily obtained, and hence the addition of about 10 ml. of carbon tetrachloride is particularly desirable. Finally distil off the carbon... 

As a general guide, however, it may be noted that the following have fairly easily recognisable odours methyl and ethyl formate methyl and ethyl acetate (apples) methyl and ethyl benzoate methyl salicylate (oil of winter-green) and ethyl salicylate methyl and ethyl cinnamate. (It is however usually impracticable to distinguish by odour alone between the methyl and ethyl esters of a particular acid.) Methyl and ethyl o. alate, and methyl and ethyl phthalate are almost odourless. Succinic and tartaric esters have faint odours. 

Phenyl-propyl alcohol, CgH. CHj. CH.2. CHj. OH, is the next highest homologue of phenyl-ethyl alcohol, and is also known as hydro-cinnamyl alcohol. Like the last described bodies it has been known for many years, its first preparation being described in the Aivnalen (188, 202). It occurs as a cinnamic acid ester in storax, and as an acetic ester in cassia oil. It is prepared synthetically by the reduction of cinnamyl alcohol with sodium amalgam and water, or by the reduction of cinnamic or benzyl acetic esters with sodium and absolute alcohol. It has the following characters —... 

Ethyl Cinnamate.—The cinnamic ester of ethyl alcohol is a natural constituent of a few essential oils, including camphor oil and storax. It is formed synthetically by condensing cinnamic acid and ethyl alcohol by dry hydrochloric acid gas. It has a soft and sweet odour, and is particularly suitable for blending in soap perfumes. It is an oil at ordinary temperatures, melting at 12°, and boiling at 271°. Its specific gravity is 1 0546, and its refractive index 1 5590. 

A study of the regioselectivity of the 1,3-dipolar cycloaddition of aliphatic nitrile oxides with cinnamic acid esters has been published. AMI MO studies on the gas-phase 1,3-dipolar cycloaddition of 1,2,4-triazepine and formonitrile oxide show that the mechanism leading to the most stable adduct is concerted. An ab initio study of the regiochemistry of 1,3-dipolar cycloadditions of diazomethane and formonitrile oxide with ethene, propene, and methyl vinyl ether has been presented. The 1,3-dipolar cycloaddition of mesitonitrile oxide with 4,7-phenanthroline yields both mono-and bis-adducts. Alkynyl(phenyl)iodonium triflates undergo 2 - - 3-cycloaddition with ethyl diazoacetate, Ai-f-butyl-a-phenyl nitrone and f-butyl nitrile oxide to produce substituted pyrroles, dihydroisoxazoles, and isoxazoles respectively." 2/3-Vinyl-franwoctahydro-l,3-benzoxazine (43) undergoes 1,3-dipolar cycloaddition with nitrile oxides with high diastereoselectivity (90% de) (Scheme IS)." " ... 

A somewhat different route is used to prepare an analogue that bears additional oxygen. The sequence, in this case, starts by base-catalyzed formylation of the hydro-cinnamic acid derivative (40-1) with ethyl formate. Condensation of the product (40-2) with guanidine in this case leads to a pyrimidone (40-3), with the cyclization involving an ester-amide interchange between guanidine and the ester. Reaction of... 

Cinnamic acid, a-cyano-/3-methyl-, ethyl ester)... 

Other preparations of 2-iminothiazolidin-4-ones which are discussed in the review by Brown139 utilize the reactions of thiourea with a-hydroxy acids,146 ethyl diazoacetate,73 glycidic esters,74,147 cinnamic acid,148 unsaturated diacids (fumaric, maleic, and citraconic) or their esters or imides,149-152 and propiolic esters.153,154 There has been considerable controversy in the literature surrounding the propiolic ester synthesis since many workers have proposed that the products are 1,3-thiazines (see Section IV, B, 1). The pertinent papers in this controversy have been summarized by Cain and Warrener.155 Nagase158 has recently settled the argument in favor of the 2-iminothiazolidin-4-... 

Peepaeation 71.—Ethyl Cinnamate [Ethyl ester of S-pkenyl-2-propen acid]. 

In the reverse case of the ethyl esters, where the alcohol derived radical is comparatively small, it is the acidic part of the molecule that dominates, as in the higher members of the series such as the benzoate, cinnamate, phenylacetate, and salicylate. Many of these higher ester radicals are very dominant in character and give rise to closely related series. Cinnamates and phenylacetates, for example, are some of the most readily recognized perfumery materials owing to their very characteristic odors. 

Ethyl dnnamate occurs in small amounts in storax.1 It has been prepared by the action of ethyl alcohol on cinnamic acid in the presence of dry hydrochloric or sulfuric acid 2 by the distillation of the copper salt of the monoethyl ester of benzylidene oxalacetic acid3 and by the condensation of ethyl acetate and benzaldehyde in the presence of sodium.4 The method described in the procedure is a slight modification of the one originally described by Claisen.5... 

The results obtained for the asymmetric 1,4-addition of arylboionic acids to crotonates or cinnamates in the presence of a Rh(acac)(C2H4)2-(S)-binap catalyst are summarized in Table 3. The ester group (R2) significantly affects the %ee. Thus, the i-propyl, cyclohexyl, (-butyl, benzyl esters achieved a high %ee whereas the methyl and ethyl esters (entries 1-4) resulted in low asymmetric induction. The absolute configuration of benzyl 3-phenylbutanoate ([a]D -14.5 (c 1.02, CHC13) obtained from (S)-binap was established to be (R) by the specific rotation reported for (R)-3-phenylbutanoic acid ([a]D -45.8 (c 0.77, benzene). 

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