Salicylic acid phenyl ester

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. 

Benzyl Salicylate, 2-Hydroxybenzoic acid phenyl methyl ester salicylic acid benzyl ester. CKH mol wt 228.24. C 73.677°, H 5.307°, O 21.03%. Prepd from sodium alkylate and benzyl chloride Volwiler, Vliet, J. Am. Chem. See 43, 1672 (1921). 

Phenyl Salicylate. 2-Hydroxybenzolc acid phenyl ester Salol. CUH 1 03i mol wt 214.21. C 72.89%, H 4.71%, O 22.41%. Made by the action of phosphorus oxychloride on a mixture of phenol and salicylic acid. 

See Phenoxyethylparaben 2-Hydroxybenzoic acid phenyl ester. See Phenyl salicylate... 

Synonyms 2-hydroxybenzoic acid phenylmethyl ester salicylic acid benzyl ester benzyl o-hydroxybenzoate 2-hydroxybenzoic acid phenyl methyl ester... 

SCHEME 31.16 Synthesis of xanthones by PER of salicylic or thiosaUcylic acid phenyl esters. 

The catalytic effect of nickel(n) on hydrolysis rates of the salicyl and phenyl esters of pyridine-2,6-dicarboxylic acid is ascribed to the intermediacy of a 1 1 complex between the ester and the nickel(n). Rates of hydrolysis and of reaction with hydroxide are reported.Kinetic and equilibrium studies have... 

However, this method is appHed only when esterification cannot be effected by the usual acid—alcohol reaction because of the higher cost of the anhydrides. The production of cellulose acetate (see Fibers, cellulose esters), phenyl acetate (used in acetaminophen production), and aspirin (acetylsahcyhc acid) (see Salicylic acid) are examples of the large-scale use of acetic anhydride. The speed of acylation is greatiy increased by the use of catalysts (68) such as sulfuric acid, perchloric acid, trifluoroacetic acid, phosphoms pentoxide, 2inc chloride, ferric chloride, sodium acetate, and tertiary amines, eg, 4-dimethylaminopyridine. 

Salicylic acid is manufactured on a large scale. In the dye industry it serves for the production of valuable azo-dyes which exhibit great fastness. To some extent these dyes are applied to mordanted fibres. In addition, the acid and its derivatives are widely used in pharmacy. Being a phenolcarboxylic acid it has a powerful disinfecting action (preservative). It has further proved itself an important antirheumatic and an analgetic. The derivative in which the phenolic hydroxyl group is acetylated (aspirin) has become especially popular. The first medicament of the series was the phenyl ester of salicylic acid, salol, which is produced as a by-product in the technical process. The preparation of salicylaldehyde has been described above (p. 235). 

Amino salicylic acid and its salts have been used in the treatment of tuberculosis. />-Amino s alicylic acid can be prepared by the carboxylation of, w-amino phenol (32). Aminosalicylic acid USP assays not less than 98.5% and not more than 100.5%, calculated on the anhydrous basis. The antitubercular agents are likely to be used as the more tolerated salts calcium [133-15-3], potassium [133-09-5], sodium [133-10-8], and the ethyl [6069-17-2] and phenyl [133-11-9] esters of aminosalicylic acid. 

Perfumes, Flavors, Cosmetics, and Soap. Many naturally occurring esters in essential oils and some synthetic esters are important fragrance and flavor compounds (61,62). They are used in perfumes, flavors, cosmetics, soaps, deteigents, and air fresheners. Benzyl, butyl, ethyl, methyl, and phenyl esters of benzoic acid are used as flavors, perfumes, and food preservatives. Glyceryl 4-aminobenzoate [13644-7] and 2-ethylhexyl 4-dimethylaminobenzoate [21245-02-3] are used in cosmetic sunscreen preparations. Alkyl esters of 4-hydroxybenzoic acid, called parabens, have been used under various names for fungus infections of the skin, and as preservatives in lotions and creams (101). Soap and cosmetic fragrances use large amounts of amyl and benzyl salicylate. Benzyl salicylate [118-58-1] is also used in deodorant sprays. 2-Ethylhexyl salicylate [118-60-5] and 2-ethylhexyl 4-methoxycinnamate [5466-77-3] are used in sunscreen formulations (102). 

Phenylis Salicylas, Phenyl Salicylate, Salol, C13H10O3, is the salicylic ester of phenyl, and occurs as a white, crystalline powder, odorless and almost tasteless, nearly insoluble in water, soluble in 10 parts alcohol, and very soluble in ether, chloroform, and oils. On warming with an alkali, it splits up into salicylic acid 60, and phenol 40, frequently repeated, in compressed tablets or in cachets, or suspended by mucilage of acacia or of tragacanth. 

SYNS BENZOIC ACID, 2-HYDROXY-, 4-METHYL-PHENYL ESTER (9CI) p-CRESYL SAUCYLATE 4-METHYLPHENYL 2-HYDROXYBENZOATE 4-METHYLPHENYL SALICYLATE SAUCYUC ACID. p-TOLYL ESTER... 

This compound will be referred to again in connection with the synthesis of salicylic acid (p. 717). The acid ester of phenol and sulphuric acid, phenyl sulphuric acid, CeHs—O—SO2OH, is a constituent of animal urine. The esters of phenols and organic acids are not readily formed by the direct action of the acids, in which respect the phenols again resemble tertiary alcohols. They may be prepared from phenols by the action of acid chlorides acid anhydrides or a mixture of the acid and phosphorus oxychloride. 

In all of these cases the carboxyl group results from the direct introduction of carbon dioxide in front of a hydrogen or sodium atom. Now the sodium compound of phenol, viz., sodium phenolate, CeHg—ONa, undergoes a similar reaction yielding first a phenyl ester of carbonic acid which rearranges into salicylic acid. 

Salol and Aspirin.— The sodium salt and several derivatives possess medicinal properties as internal antiseptics as antipyretics or temperature reducers, and to lessen the pain of rheumatism. The most common of these are salol, which is the phenyl ester of salicylic acid, as an acid, and aspirin, which is the acetic acid ester of salicylic acid, as a phenol. 

Salol is used as an intestinal antiseptic. It is prepared by heating salicylic acid alone to 160° to 240°. In this case one molecule loses carbon dioxide yielding phenol which then esterifies with another molecule of the acid yielding the phenyl ester. 

A) Acetylsalicylic Add (Aspirin). Salicylic acid and its derivatives were among the first synthetic organic compounds to be used for therapeutic purposes. The sodium salt of salicylic acid, the methyl and phenyl esters, and the acetyl derivative of salicylic acid are extensively used to diminish pain (as analgesics) and to reduce the temperature of the body (as antipyretics). The most widely used is the acetyl derivative which is sold under the name aspirin. Salicylic acid is prepared industrially by the carbonation of sodium phenoxide, at 180-200° at atmospheric pressure or 120-130° at a pressure of a few atmospheres. 

The salicylanilides may also be conveniently synthesized by reaction of salicylic acid with aniline in the presence of P2O5 [58], tetraalkylpyrophosphite [59,60], Me2As(0)0H [61], H3PO4 or H4P2O7 [62] or DCC [45]. In another approach salicylic acid is converted into the phenyl ester (37), which is heated witli appropriate aniline at high temperatures to yield the corresponding salicylanilides [63-65]. 

Benzoic acid, 4-(((ethylphenylamino) methylene) amino)-, ethyl ester. See N-(p-Ethoxycarbonylphenyl)-N-ethyl-N-phenylformamidine Benzoic acid, 2-hydroxy-, 4-(1,1-dimethylethyl) phenyl ester. See p-t-Butylphenyl salicylate Benzoic acid nitrile. See Benzonitrile Benzoic acid sodium salt. See Sodium benzoate Benzoic acid, tetraester with 2,2-bis (hydroxymethyl)-1,3-propanediol Benzoic acid, tetraester with pentaerythritol. See Pentaerythrityl tetrabenzoate... 

Nitro compounds, ar. Nitrobenzene, m-Dinitrobenzene o-Nitrophenol N-Nitramines Oxonium fluoroborate Trialky loxonium salt Trialky loxonium fluoroborate Pyrylium fluoroborate Carboxylic acid esters HCOOC Hs, p-Nitro-phenyl formate Isopropenyl acetate Salicylic acid esters Ethyl cyanoacetate Chloroformic acid esters Ethyl chloroformate, ClCOOC Hg-i Methyl trichloroacetate Diethyl oxalate Ethyl malonate... 

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