Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Chemical compound
Anisole, or methoxybenzene, is an organic compound with the formula CH3OC6H5. It is a colorless liquid with a smell reminiscent of anise seed, and in fact many of its derivatives are found in natural and artificial fragrances. The compound is mainly made synthetically and is a precursor to other synthetic compounds. Structurally, it is an ether (−O−) with a methyl (−CH3) and phenyl (−C6H5) group attached. Anisole is a standard reagent of both practical and pedagogical value.[2]
It can be prepared by the Williamson ether synthesis; sodium phenoxide is reacted with a methyl halide to yield anisole.
^ abcNomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. pp. 702–703. doi:10.1039/9781849733069-00648. ISBN 978-0-85404-182-4. Anisole, C6H5−O−CH3, is the only name in the class of ethers which is retained both as a preferred IUPAC name and for use in general nomenclature. For preferred IUPAC names, no substitution is allowed; for general nomenclature substitution is allowed on the ring and on the side chain under certain conditions (see P-34.1.1.4).
^Smith, Michael B.; March, Jerry (2007), Advanced Organic Chemistry: Reactions, Mechanisms, and Structure (6th ed.), New York: Wiley-Interscience, ISBN 978-0-471-72091-1
Anisole, or methoxybenzene, is an organic compound with the formula CH3OC6H5. It is a colorless liquid with a smell reminiscent of anise seed, and in...
considering the structure as either an acetyl (methyl-ketone) analog of anisole. Other names It can also be seen as a methyl ether analog of acetophenone...
(t-butylhydroquinone), a preservative made infamous by food writer Michael Pollan. Anisole Butylated hydroxytoluene (BHT) "BHA and BHT". Archived from the original...
diethyl ether, dipropyl ether etc. Illustrative unsymmetrical ethers are anisole (methoxybenzene) and dimethoxyethane. Vinyl- and acetylenic ethers are...
donors tend to induce ortho protonation, as shown in the reduction of anisole (1). Electron-withdrawing substituents tend to induce para protonation...
methylating agent. A wide variety of phenols undergo O-methylation to give anisole derivatives. This process, catalyzed by such enzymes as caffeoyl-CoA O-methyltransferase...
regarding the synthesis of ethers can be applied to phenol ethers as well. Anisole (C6H5OCH3) is the simplest phenol ether, and is a versatile precursor for...
compounds are methanol and dimethyl ether. Other methoxy ethers include anisole and vanillin. Many metal alkoxides contain methoxy groups, such as tetramethyl...
Estragole (p-allylanisole, methyl chavicol) is a phenylpropene, a natural organic compound. Its chemical structure consists of a benzene ring substituted...
In electrophilic aromatic substitution reactions, existing substituent groups on the aromatic ring influence the overall reaction rate or have a directing...
including formaldehyde, acetic acid, methyl tert-butyl ether, methyl benzoate, anisole, peroxyacids, as well as a host of more specialised chemicals. Small amounts...
treated with diazomethane in the presence of boron trifluoride (BF3), anisole is obtained as the main product and nitrogen gas as a byproduct. C6H5OH...
sulfur analogue—the thioether rather than the oxygen-centered ether—of anisole. It can be prepared by methylation of thiophenol. Alkyllithium reagents...
comprising magnesium oxide or alumina. Temperatures above 300 °C are typical. Anisole converts to cresols under these conditions. Another isomer of cresol is...
o-alkylation is methoxybenzene, better-known as anisole, and water, which is not shown in the diagram. Anisole is listed as an acute hazard to aquatic life...
Friedel-Crafts acylation of benzene, with an aluminium chloride catalyst: With anisole, it is used for the synthesis of venlafaxine. Like other acyl chlorides...
143. doi:10.15227/orgsyn.058.0143. G. S. Hiers and F. D. Hager (1941). "Anisole". Organic Syntheses; Collected Volumes, vol. 1, p. 58. H. Perst; D. G....
with P4S10, including alcohols and amines. Aromatic compounds such as anisole, ferrocene and 1-methoxynaphthalene react to form 1,3,2,4-dithiadiphosphetane...
prepared commercially from 4-methoxypropiophenone, which is prepared from anisole. Anethole is distinctly sweet, measuring 13 times sweeter than sugar. It...
diverse routes in the laboratory. o-Anisidine, derived in two steps from anisole, can be hydrolyzed via its diazonium derivative. Guaiacol can be synthesized...
selective and especially helpful in production of aromatic ethers such as anisole which has increasing industrial applications. Since alkoxide ions are highly...
commonly called thioanisole, since its structure is related to that for anisole, C6H5OCH3. The modern systematic nomenclature in chemistry for the trival...
5-η)-2-Methoxy-2,4-Cyclohexadien-1-yl]Iron(1+) Hexafluorophosphate(1−) from Anisole". Organic Syntheses; Collected Volumes, vol. 6, p. 996. Kovarik, Bill (1994)...
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