Salicylic acid methyl ether

Synonyms O-anisyl acid, o-methoxybenzoic acid, salicylic acid methyl ether, 2-methxy benzoic acid, 2-anisic acid, etc. 

Salicylic acid methyl ether. See o-Anisic acid Salicylic acid octyl ester. See Octyl salicylate Salicylic acid pentyl ester. See Amyl salicylate Salicylic acid, potassium salt. See Potassium salicylate... 

Methoxybenzoic acid (o- Anisic acid Salicylic acid methyl ether) 100 1 200 113 129 ... 

SALICYLALDEHYDE METHYL ETHER see AOT525 SALICYLIC ACID see SAIOOO m-SALICYUC ACID see HJIlOO SALICYLIC ACID, 3,5-DINITRO- see HKE600 SALICYLIC ACID, ISOBUTYL ESTER see IJNOOO SALICYLIC ACID, ISOPENTYL ESTER see IMEOOO SALICYLIC ACID, METHYL ESTER see MPIOOO SALICYLIC ACID with PHYSOSTIGMINE (1 1) see PIA750... 

After evaporation of the solvent the products of reaction are purified by distillation, or, if they are solid, by crystallisation. Use one of the phenols available in the laboratory and report on the nature of the methyl ether obtained. Treat carboxylic acids (p-toluic, phenylacetic, cinnamic, oxalic, terephthalic, salicylic, etc.) in the same way. 

A mixture of 5-chloromethyl salicylate, 3-chloro-2-methylpropene, potassium carbonate, and acetone was heated at reflux overnight. After cooling, the mixture was extracted with diethyl ether and ethyl acetate. The organic extracts were combined, washed twice with a 10% sodium chloride solution and water, dried over sodium sulfate, and concentrated in vacuum. The resulting liquid was vacuumed distilled. The fraction collected and the desired 5-chloro-2-(2-methyl-2-propenyloxy)benzoic acid, methyl ester was obtained. 

Selenazoles (72) and methyl salicylate or methyl-o-mercaptobenzoate lead to ethers (77) or thioethers (78). The acid chlorides of (77) and (78) through a Friedel-Craft cyclization afford l-benzoxepino[3,4-d]selenazoles (79) and l-benzothiepino[3,4-d]selenazoles (80), respectively (Scheme 28) (81JHC789). 

Esters.— The simplest class of compounds present in essential oils are the esters or ethereal salts (p. 140). In our early discussion of these compounds in the aliphatic series it was stated that the odor and flavor of common fruits is probably due to ester compounds and that certain empirical mixtures of esters are used as artificial fruit essences. Artificial apple essence, for example, may be prepared by mixing certain proportions of ethyl nitrite, ethyl acetate and amyl valerate with chloroform, aldehyde and alcohol. An example of an essential oil which consists of a single ester is oil of wintergreen. vAdxh is the methyl ester of salicylic acid, ortho-hydroxy benzoic acid (p. 714). 

In some cases, a stoichiometric amount of the base was employed to facilitate isolation of the product by precipitation of its salt. For instance, the sodium salt of 2-act -nitropropane-l,3-diol (18) was prepared in >95% yield of isolated product starting from nitromethane and paraformaldehyde in a 1 2 ratio by using 1.2 equiv. of sodium methoxide in methanol. The successive protonation of (18) was achieved in 75% yield by quick addition of salicylic acid in f-butyl methyl ether. These highly satisfying results in preparing 2-nitropropane-l,3-diol (15), key intermediate for NPP synthesis, stem also from adequate control of temperatures and reaction times, dilution of the reaction mixtures and choice of solvents. 

Salicylic acid O-methyl ether has been submitted to the Birch reduction and the product methylated. This sequence is reminiscent of the synthesis of... 

The conversion from salicylic acid to methyl 2-methoxybenzoate could best be carried by treating salicylic acid with a quantitative amount of diazomethane (CH2N2) This versatile reagent reacts with both carboxylic acids and phenols to give methyl esters and methyl ethers respectively. The mechanism of these conversions is based upon the acidity of carboxylic acids and phenols. (Alcohols normally do not react with diazomethane.)... 

In 1834, codeine was isolated from opium by Pierre Jean Robiquet (1780-1840). One year later, Pierre-Joseph Pelletier (1788-1842) and M. Thiboumery discovered thebaine (named after the ancient Egyptian city of Thebes). In 1848, at the University of Giessen, papaverine was extracted from poppy waste by Georg Merck (1825-1873), the son of Heinrich Emanuel Merck. In 1870, Augustus Matthiessen (1831-1870) and Charles R. A. Wright (1844-1894) recognised that codeine is the monomethyl ether of morphine. After the selective methylation of morphine for the preparation of codeine had failed, Felix Hoffmann (1868-1946) tried out in 1897 a selective acetylation, in analogy to the synthesis of aspirin from salicylic acid. [91]... 

Phenethyl salicylate Phenethyl tiglate Phenoxyacetaldehyde Phenoxyacetic acid Phenoxyethyl isobutyrate Phenoxyethyl propionate Phenylacetaldehyde Phenylacetaldehyde dimethyl acetal Phenylacetaldehyde glyceryl acetal Phenylacetaldehyde glyceryl cyclic acetals Phenylacetic acid Phenylacetonitrile o-Phenyl anisole 2-Phenylethyl acetate 2-Phenylethyl methyl ether... 

In leaves extracts, the main constituents included Salicylic acid (14.466%), Ethanol,(2-(3,4-dihydroxyphenyl)-(13.254%), Catechol Monoethyl Ether (7.577%), Benzeneacetic acid, a-hydroxy-, methyl ester (6.151%), Patchouli alcohol (5.130%), 5-Methyl-2,4-diisopropylphenol (3.316%), 4-Hydroxyphenylethanol (2.799%), Hexanoic acid,6-iodo-(2.730%), 1-Phenylethanol (2.351%), Benzeneacetic acid (2.164%), Methylbenzene (1.570%), Octacosane (1.517%), n-Pentadecanoic acid (1.504%), 9-Methyl-Z-lO-tetradecen-l-ol acetate (1.457%), 1-Hexacosene (1.359%), j -Hydroxybenzoic acid (1.001%). 

In the presence of salicylic acid the powder must first be treated with dilute alkali, filtered, acidified and extracted with ether before determining the boric acid in the aqueous residues. In the absence of zinc oxide, boric acid can be titrated directly in the presence of zinc oxide the boric acid is extracted with cold water for titration and the zinc oxide determined in the water-insoluble portion by solution in an excess of N acid and back titration with alkali to methyl orange in the presence of 2 g of ammonium chloride. 

The B,P.C, method of assay dissolves the boric acid and salicylic acid with dilute alkali followed by filtration. The salicylic acid is extracted as usual with ether after acidification and after evaporation of the ether is determined by titration with sodium hydroxide in ethanolic solution. The boric acid is titrated in the aqueous residue after neutralisation to methyl orange. 

Bis(salicylic acids) have been polymerized with metal salts to yield the chelate polymers (lX-26). Metal acetylacetonates (72), and metal chlorides and acetates have been used. Aqueous (9, 99,131) or organic (72) media are suitable. Data indicating that high molecular weight products were obtained have not been presented. The insolubility of the products is the main reason. A comparative study of the polymerization of a free bis(salicylic acid), the corresponding bis(methyl salicylate), and the corresponding bis(methyl ether salicylic acid) has been reported (72). 

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