Trans-Cinnamic acid ester

SYNS BENZYL ALCOHOL CINNAMIC ESTER BENZYL y-PHENYLACRYLATE Q CINNAMEIN trans-CINNAMIC ACID BENZYL ESTER FEMA No. 2142 3-PHENYL-2-PROPENOIC ACID PHENYLMETHYL ESTER (9CI)... 

Study, dimerization would not occur (Scheme 1-a.). Therefore, the molecules of the 5 reactant pair must undergo a rotation so that a favorable overlap between the orbitals can occur (scheme 1-b) and lead to the formation of the 5 dimer. It is difficult to rationalize why the 5 dimer is formed only from cation 1 and the e dimer is formed only in homogeneous solution from cation 2. There is precedent for the formation of the 5 dimer in the solid state. Previous work in our laboratory indicates that the dioctadecyl ester of S-truxinic acid is formed by irradiation of C crystals of the octadecyl ester of trans cinnamic acid (32). 

Benzyl Cinnamate. 3-Phenyl-2-propenoic acid pbtnylmelhyl ester trans-cinnamic acid benzyl ester cinna-mein. CjjH tO, mol wt 238.27. C 80.65%, H 5.92%, O 13.43%. C(H5CH—CHOOOCHjCjHj. Constituent of sto-rax, Peru and Tolu balsams Tsehirch, Trog, Arch. Pharm. 232, 70 (1894) Tsehirch, Oberlander. ibid. 559. Prepn Volwiler, Vlict, J. Am. Chem. Soc. 43, 1672 (1921) Elicl. Anderson, ibid. 74, 547 (1952) Bender. Zerner, ibid. 84, 2550 (1962). 

Damen and Neckers (111) were more successful in this respect. They also used cyclobutane derivatives and copolymerized the bis(vinylbenzyl)ester of a-truxillic acid, 3 truxinic acid, and 6-truxinic acid. After removing the template, trans-cinnamic acid was bound to each pair of benzyl alcohols in a cavity. Irradiation of the polymers yielded dimerization of the trans-cinnamic acid. Table VIII shows the composition of the products from hydrolysis of the polymers. 

Synonyms Benzyl alcohol cinnamic ester Benzyl y-phenylacrylate Benzyl 3-phenylpropenoate Benzyl 3-phenyl-2-propenoate Cinnamein trans-Cinnamic acid benzyl ester Phenylmethyl 3-phenyl-2-propenoate 3-Phenyl-2-propenoic acid phenylmethyl ester Definition Ester of benzyl alcohol and cinnamic acid, found in balsams of Peru, Tolu, Styrax, Copaiba and others Empirical C16H14O2... 

See Diethylene glycol diacrylate 2-Propenoic acid, 2-phenoxyethyl ester. See 2-Phenoxyethyl acrylate 2-Propenoic acid, 3-phenyl-, (E)-. See trans-Cinnamic acid... 

Table III shows the results of hydro-bromination and hydrochlorination of the ethyl trans-cinnamate inclusion complexes. No hydrochlorination was observed at various temperatures after long exposure of hydrogen chloride gas similar to the reaction of trans-cinnamic acid [14]. Addition of hydrogen bromide to the ester gave an optically active and regioselective product, ethyl R-(+)-3-bromo-3-phenyl-propanoate in 46 % e.e. from the a-cyclodextrin, or ethyl S-(-)-3-bromo-3-phenylpropanoate in 31 % e.e. from the 3-cyclodextrin inclusion complex.

C1SH20O2 tran -cinnamic acid hexyl ester 3488-00-4... 

C12H12 02 trans-cinnamic acid allyl ester 1866-31-5... 

C12H14 02 trans-cinnamic acid isopropyl ester 60512-85-8... 

C12H14 02 trans-cinnamic acid propyl ester 74513-58-9 ... 

C14H18 02 trans-cinnamic acid pentyl ester 3487-99-8... 

C17H24 02 trans-cinnamic acid octyl ester 69038-78-4... 

C21H32 02 trans-cinnamic acid dodecyl ester 96059-66-4... 

The addition of benzonitrile oxide to acrylic acid gave only the 4-carboxylic acid (441) (59MI41601), while addition to cis- and trans-cinnamic esters gave cis and trans diastereomeric pairs of 4-carboxylic acids (442) (Scheme 100) (59MI41600). Arbisono repeated the experiment and, when methyl c/s-cinnamate was used, in addition to the 4-carboxylic acid some 5-carboxylic acid (442) was isolated (66MI41600). The reaction of vinyl bromides with benzonitrile oxide yielded only an isoxazole and not a bromoisoxazoline (Scheme 101) (78JCR(S)192). 

There are several examples in the literature where similar cis-trans isomerizations of o-hydroxy cinnamic acid derivatives have been used to deliver fragrances. For example, ester 76, which was absorbed into cloth and exposed to sunlight, released its fragrant alcohol moiety, whereas samples that were stored in the dark did not... 

Pr, Bu, Ph etc) to benzonitrile oxide are oxidized to trans-4-hydroxy-2-isoxazolines 10 by t-butyl hydroperoxide (94TL7493). A reversal of regiochemistry was observed in the reaction of aromatic nitrile oxides with derivatives of cinnamic acid the methyl ester gave a mixture of the esters 11 and 12 (R = OMe), in which the former predominated, while in the case of M,N-diethylcinnamide the amide 12 (R = NEt2) was the main product (94TL6473). 

Unsaturated side-chains are present in the cinnamic acids, some of which occur naturally in the trans form 12. Syntheses of the acids and their esters by the Claisen condensation and the Perkin and Knoevenagel reactions are discussed in Chapter 6. 

Which of the two is the cis form and which the trans form has not been determined. A third cinnamic acid, viz., iso-cinnamic acid, is also known, but the constitution of it has not been established. Cinnamic acid is found in nature in the resin storax both as the free acid and as the cinnamic alcohol ester, styrin. It is also found in Peru and Tolu balsams as the free acid and as the benzyl alcohol ester, the benzoic acid ester of benzyl alcohol being present also. Thus benzyl alcohol, benzoic acid, cinnamic alcohol and cinnamic acid are all constituents of esters present in these plant resins. Allo-cinnamic acid, the geometric isomer, is obtained from coca leaves from which the alkaloid cocaine is also obtained (p. 896). When cinnamic acid is heated with lime it loses carbon dioxide and yields the unsaturated side-chain hydrocarbon st3rrene, or phenyl ethylene, CeHs—CH = CH2. On reduction it yields first cinnamic aldehyde, found in oil of cinnamon (p. 842) and then cinnamic alcohol. Both cinnamic acid and allo-cinnamic acid yield anhydrides. 

Unsaturated Lignin Model Compounds Double bonds in lignin model compounds are attacked by peracetate ions. Dehydro-di-woeugenol (XXI, Figure 12.9) reacted with epoxidation of the aliphatic double bond and formation of the diol. The double bonds in stilbenes [59] and coniferaldehyde [90] are also cleaved. FemUc acid (IVa) and its ethyl ester reacted slowly at 50°C the methyl ether, 3,4-dimethoxy cinnamic acid, was much less reactive and was almost quantitatively recovered [55]. The reactions of ferulic acid and its ethyl ester (both in the trans form) were accompanied by trans-cis isomerization, perhaps an indication of reversible phenoxy radical formation. HomovanilUc acid (XXXa) was also formed the proposed mechanism involved epoxidation of the a-P double bonds followed by decarboxylation. 

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