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Benzyl alcohol and β‐phenethyl alcohol (2‐phenylethanol) are the simplest of the aromatic alcohols, and, as such, are chemically similar. Benzyl alcohol occurs widely in essential oils both as the free alcohol, and, more importantly from a fragrance standpoint, in the form of various esters. Although benzyl alcohol itself is rather bland in odor, combined with its much more fragrant esters it is an important part of the odor of jasmine, ylang‐ylang, gardenia, some rose varieties, narcissus and peony, as well as castoreum, balsams of peru and tolu, and propolis. Benzyl alcohol occurs primarily in flower oils and tree exudates. Benzyl alcohol readily undergoes the reactions characteristic of a primary alcohol, such as esterification and etherification, as well as halide formation. In addition, it undergoes ring substitution. Today benzyl alcohol is almost universally manufactured from toluene which is first chlorinated to give benzyl chloride. This is then hydrolyzed to benzyl alcohol by treatment with aqueous sodium carbonate. In the soap, perfume, and flavor industries benzyl alcohol is primarily used in the form of its aliphatic esters. Benzyl alcohol is commercially available in five grades. The largest proportion of benzyl alcohol is for use in the photographic and textile industries although the latter use has been declining. The textile grade is used as a dyeing assistant for wool and nylon. The pharmaceutical industry makes use of benzyl alcohol's local anesthetic, antiseptic, and solvent properties. The technical grade of benzyl alcohol is used in rug cleaners as a degreasing agent, in leather dyeing, in ballpoint inks, as a cleaner for soldering, and as an extractive distillation solvent for xylenes and cresols. In addition, benzyl alcohol is used extensively in the polymer industry and in the manufacture of automobile tires. This material has a Generally Recognized As Safe (GRAS) status indicated by the Flavor and Extract Manufacturers' Association for use in flavors and by the Council of Europe for use as a flavor. Benzyl alcohol satisfies the most current guidelines published by the International Fragrance Association (IFRA). Of all the aromatic organic molecules β‐phenethyl alcohol (PEA) is probably the most prestigious aroma chemical in the world of perfumery. This is because of its exquisite odor of natural rose petals. The compound undergoes the usual chemical reactions of alcohols or aromatic compounds. In insect control, PEA has been considered as a mosquito repellant. The alcohol also has antifungicidal properties. Because of factors of low cost, stability, and odor quality, PEA is ideally suited for use in bar soap fragrances. Current commercial methods for making PEA include Grignard synthesis, Friedel‐Crafts process, and catalytic hydrogenation of styrene oxide. Approximately 85% of the PEA is employed for fragrance use. The use of β‐phenethyl alcohol generally presents no health problems.
Benzyl alcohol and β‐phenethyl alcohol (2‐phenylethanol) are the simplest of the aromatic alcohols, and, as such, are chemically similar. Benzyl alcohol occurs widely in essential oils both as the free alcohol, and, more importantly from a fragrance standpoint, in the form of various esters. Although benzyl alcohol itself is rather bland in odor, combined with its much more fragrant esters it is an important part of the odor of jasmine, ylang‐ylang, gardenia, some rose varieties, narcissus and peony, as well as castoreum, balsams of peru and tolu, and propolis. Benzyl alcohol occurs primarily in flower oils and tree exudates. Benzyl alcohol readily undergoes the reactions characteristic of a primary alcohol, such as esterification and etherification, as well as halide formation. In addition, it undergoes ring substitution. Today benzyl alcohol is almost universally manufactured from toluene which is first chlorinated to give benzyl chloride. This is then hydrolyzed to benzyl alcohol by treatment with aqueous sodium carbonate. In the soap, perfume, and flavor industries benzyl alcohol is primarily used in the form of its aliphatic esters. Benzyl alcohol is commercially available in five grades. The largest proportion of benzyl alcohol is for use in the photographic and textile industries although the latter use has been declining. The textile grade is used as a dyeing assistant for wool and nylon. The pharmaceutical industry makes use of benzyl alcohol's local anesthetic, antiseptic, and solvent properties. The technical grade of benzyl alcohol is used in rug cleaners as a degreasing agent, in leather dyeing, in ballpoint inks, as a cleaner for soldering, and as an extractive distillation solvent for xylenes and cresols. In addition, benzyl alcohol is used extensively in the polymer industry and in the manufacture of automobile tires. This material has a Generally Recognized As Safe (GRAS) status indicated by the Flavor and Extract Manufacturers' Association for use in flavors and by the Council of Europe for use as a flavor. Benzyl alcohol satisfies the most current guidelines published by the International Fragrance Association (IFRA). Of all the aromatic organic molecules β‐phenethyl alcohol (PEA) is probably the most prestigious aroma chemical in the world of perfumery. This is because of its exquisite odor of natural rose petals. The compound undergoes the usual chemical reactions of alcohols or aromatic compounds. In insect control, PEA has been considered as a mosquito repellant. The alcohol also has antifungicidal properties. Because of factors of low cost, stability, and odor quality, PEA is ideally suited for use in bar soap fragrances. Current commercial methods for making PEA include Grignard synthesis, Friedel‐Crafts process, and catalytic hydrogenation of styrene oxide. Approximately 85% of the PEA is employed for fragrance use. The use of β‐phenethyl alcohol generally presents no health problems.
Im System der Phenylessigsaure (11) erfolgt unter der Einwirkung von s-Triazin (I) durch zweifache Aminomethinylierung und anschlieI3ende Cyclisierung Bildung 5-substituierter 4-Hydroxy-pyrimidine (VI). Als Sekundamaktion des aus Phenylessigsaure-anhydrid (IX) und I primar gebildeten Aminomethinylierungsproduktes (X) tritt Bildung von 4-Hydroxy-3,5-diphenyl-pyridin (XIV) auf. Letzteres entsteht auch aus I und a,a'-Diphenyl-aceton (XV). Die aus dem Enol XVIII und I gebildete 0-Aminomethinylierungsstruktur XXII geht eine Chapman-Umlagerung unter Bildung der korrespondierenden Forrnaminoverbindung XXVII ein. Reaction Behavior of Phenylacetic Acid Derivatives in AminomethinylationIn the system of phenylacetic acid (11) twofold aminomethinylation takes place under the action of s-triazine (I) followed by cyclisation and formation of 5-substituted 4-hydroxypyrimidines (VI). As a secondary reaction of the aminomethinylation product X, formed from phenylacetic acid anhydride (IX) and I in a primary reaction, formation of 4-hydroxy-3,5-diphenyl-pyridine (XIV) occurs. The latter is formed also from I and a,a'-diphenylacetone (XV). The 0-aminomethinylation structure XXII formed from the enol XVIII and I undergoes a Chapman rearrangement with formation of the corresponding formamino compound XXVII.Die durch s-Triazin (I) initiierte und von Sekundarreaktionen gefolgte Anunoniethinylierung h a t im System des Phenylacetonitrils zu speziellen heterocyclischen Strukturen gefuhrt, die pharmazeutisches Interesse beanspruchenl). I n diese Versuche sind nun im Hinblick auf das Aktivierungsvermogen, das Carbonsauregruppierungen auf Grund ihres starlien (+ P)-Effektes gegenuber Methylengruppen aufweisen, auch Phenylessigsaurederivate einbezogen worden. Unter dem Gesichtspunkt des aktivierenden Substituenteneinflusses warf sich hier zunachst die Frage auf, wie der zwischen dem leicht rengierenden Malonslure-diiithylester2) und dem viillig inaktiven Diphenylmethanl) stehende Phen ylessigsaire-athyleater (I1 a ) sich gegenuber I verhalten wurde. Es zeigte sich, da13 in Pyridin allein keine Reaktion erfolgt, eine solche aher durch Zuvatz von Piperidin katalysiert werden kann. Als Primarschritt des Renktionsgeschehens ist der ziir Bildung der Aminomethin-
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