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Anisole, or methoxybenzene, is an organic compound with the formula CH 3 OC 6 H 5. 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 .
Anisole (C 6 H 5 OCH 3) is the simplest phenol ether, and is a versatile precursor for perfumes and pharmaceuticals. [1] Vanillin and ethylvanillin are phenol ether derivatives commonly utilized in vanilla flavorings and fragrances, while diphenyl ether is commonly used as a synthetic geranium fragrance.
Anisaldehyde is prepared commercially by oxidation of 4-methoxytoluene (p-cresyl methyl ether) using manganese dioxide to convert a methyl group to the aldehyde group. It can also be produced by oxidation of anethole, a related fragrance that is found in some alcoholic beverages, by oxidative cleavage of an alkene. [3]
Lawesson's reagent is commercially available. It can also be conveniently prepared in the laboratory by heating a mixture of anisole with phosphorus pentasulfide until the mixture is clear and no more hydrogen sulfide is formed, [2] then recrystallized from toluene or xylene. Samples give a strong odor of hydrogen sulfide owing to partial ...
The reaction is known to be third order – first order in the aromatic, first order in the alkali metal, and first order in the alcohol. [4] This requires that the rate-limiting step be the conversion of radical anion B to the cyclohexadienyl radical C. Birch reduction of anisole. That step also determines the structure of the product.
In order for the S N 2 reaction to take place there must be a good leaving group which is strongly electronegative, commonly a halide. [4] In the Williamson ether reaction there is an alkoxide ion (RO −) which acts as the nucleophile, attacking the electrophilic carbon with the leaving group, which in most cases is an alkyl tosylate or an ...
4-Bromoanisole forms a Grignard reagent, [1] which reacts with phosphorus trichloride to give tris(4-methoxyphenyl)phosphine: . 3 CH 3 OC 6 H 4 MgBr + PCl 3 → (CH 3 OC 6 H 4) 3 P + 3 MgBrCl
Nucleophiles displace the chloride adjacent to the nitro group: ammonia gives the aniline derivative, aqueous base gives the phenol derivative, and methoxide gives the anisole derivative. These compounds are respectively 4-chloro-2-nitroaniline, 4-chloro-2-nitrophenol, and 4-chloro-2-nitroanisole.