Benzyl alcohol cinnamic 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)... 

Benzyl alcohol cinnamic ester. See Benzyl cinnamate... 

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... 

Nearly all uses and appHcations of benzyl chloride are related to reactions of the active haUde substituent. More than two-thirds of benzyl chloride produced is used in the manufacture of benzyl butyl-phthalate, a plasticizer used extensively in vinyl flooring and other flexible poly(vinyl chloride) uses such as food packaging. Other significant uses are the manufacture of benzyl alcohol [100-51-6] and of benzyl chloride-derived quaternary ammonium compounds, each of which consumes more than 10% of the benzyl chloride produced. Smaller volume uses include the manufacture of benzyl cyanide [140-29-4], benzyl esters such as benzyl acetate [140-11-4], butyrate, cinnamate, and saUcylate, benzylamine [100-46-9], and benzyl dimethyl amine [103-83-8], and -benzylphenol [101-53-1]. In the dye industry benzyl chloride is used as an intermediate in the manufacture of triphenylmethane dyes (qv). First generation derivatives of benzyl chloride are processed further to pharmaceutical, perfume, and flavor products. 

Benzyl alcohol, C Hj. CHjOH, is the lowest member of the normal series of aromatic alcohols containing the benzene nucleus. It exists to a certain extent in the free state, but more often in the form of esters, principally of acetic, benzoic, and cinnamic acids, in a number of essential oils, such as those of jasmin, tuberose, cassie fiowers, and ylang-ylang. 

Benzyl Ginnamate.—The cinnamic acid ester of benzyl alcohol is a natural constituent of storax, tolu, and Peru balsams. It is a crystalline Bubstance with a characteristic sweet balsamic odour. It may be prepared by heating sodium cinnamate, alcohol, and benzyl chloride together under a reflux condenser. It is a useful ester where a sweet balsamic odour is required to be introduced into a perfume, especially cf the heavy type. It forms white, glistening prisms, which melt at 39°, and.decompose when heated to 350°. The best commercial specimens have the following characters —... 

Phenethyl alcohol is qualitatively and quantitatively one of the most important fragrance substances that belongs to the class of araliphatic alcohols. Its lower homologue (benzyl alcohol) and higher homologue (dihydrocinnamic alcohol) also have characteristic odor properties, but are more frequently used in the form of their esters. Cinnamic alcohol, the most important unsaturated araliphatic alcohol, is valuable for both fragrances and flavors. 

The combination of these compounds will generate cinnamic acid through the synthetic sequence illustrated below. As shown, benzyl alcohol is oxidized to benzal-dehyde using the Swem oxidation. Next, the aldehyde is reacted with triethyl phosphonoacetate by applying the Homer-Emmons reaction. Finally, the ester is hydrolyzed to a carboxylic acid. With arrow pushing, the mechanism for the... 

Homologues.—The homologues of benzyl alcohol result from substitution of the hydroxyl group in one of the methyl groups of xylene, mesitylene, etc., or, as in the examples previously given of secondary and tertiary aromatic alcohols, by the substitution of hydroxyl in a poly-carbon side chain either saturated or unsaturated. These need not be discussed further except to mention that both phenyl propanol, CeHs—CH2—CH2—CH2OH, and phenyl propenol, CeHs—CH = CH— CH2OH, are also found as cinnamic acid esters in storax. 

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. 

Benzyl Alcohol, NF. Ben/yl alcohol (phenylcarbinol. phenylmethanol) occurs naturally as the unesteriried form in oil of jasmine and in esters of acetic, cinnamic, and benzoic acids in gum benzoin,. storax re.sin. Peru balsam, tolu balsam, and some volatile oils. It is. soluble in water and alcohol and is a clear liquid with an aromatic odor. 

Dehydration. a-Substituted cinnamic esters are obtained stereoselectively from the benzylic alcohols [an/t-alcohols -> (E)-alkenes iyn-alcohols -> (Z)-alkenes]. 

Benzyl Alcohol, C6H5CH2OH, occurs in the balsam of Peru in the free condition, and in combination as the esters of benzoic acid and cinnamic acid. It is also present in small quantity in the volatile oil of cherry-laurel. The alcohol is a liquid, which possesses a faint odor, is difficultly soluble in water, and boils at 206 . 

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. 

Isopentane thiol. See 3-Methyl-1-butanethiol Isopentanoic acid. See Isovaleric acid Isopentanoic acid, phenylmethyl ester. See Benzyl isovalerate Isopentanol. See Isoamyl alcohol lsopent-2-enyl acetate. See Prenyl acetate Isopentyl acetate. See Isoamyl acetate Isopentyl alcohol. See Isoamyl alcohol s-lsopentyl alcohol. See 3-Methyl-2-butanol Isopentyl alcohol acetate. See Isoamyl acetate Isopentyl alcohol, cinnamate. See Isoamyl cinnamate... 

The aroma of peaches is characterized by y-lactones (C6-C12) and 5-lactones (Cio and Cl2). The main compound in the lactone fraction is (R)-l,4-decanolide, which has a creamy, fruity, peach-like odor. Other important compounds should be benzaldehyde, benzyl alcohol, ethyl cinnamate, isopentyl acetate, linalool, a-terpineol, a- and 3-ionone, 6-pentyl-a-pyrone (Formula 18.39, VIII), hexanal, (Z)-3-hexenal, and (E)-2-hexenal. Aroma differences in different varieties of peaches are correlated with the different proportions of the esters and monoterpenes. In the case of nectarines (Prunus persica L., Batsch var. nucipersica Schneid), the lactones y-C8-Ci2 and 5-Cio belong to the compounds with the highest aroma values. 

The basic flavour of peaches Persica vulgaris, syn. Prunus persica, Rosaceae) is typified by the presence of y-lactones (Cg-Cjj) and 8-lactones (C q and Cjj). Individual varieties differ mainly in their content of esters and monoterpenoids. As with all stone fruits, an important component is benzaldehyde, while other important compounds include benzyl alcohol, ethyl cinnamate, isopentyl acetate, hnalool, a-terpineol, hexanal, (Z)-hex-3-enal, ( )-hex-2-enal and decomposition products of carotenoids. 

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 —... 

This oil consists principally of benzyl cinnamate and benzyl benzoate, with a small amount of free benzoic and cinnamic acids. Dihydro-benzoic acid is also probably present in the form of esters. Cinnamic alcohol, vanillin, and farnesol are also present in very small amoilnt. 

The principal odorous constituent of the oil is styrol, or phenylethy-lene OgHj. CH. - CH, an optically inactive hydrocarbon boiling at 146. The cinnamic acid esters of ethyl, benzyl, phenyl-propyl, and cinnamyl alcohols are also present, as well as the free alcohols, and traces of vanillin. 

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