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Benzyl ethers are often derived from benzyl chloride. Benzyl chloride reacts with aqueous sodium hydroxide to give dibenzyl ether. In organic synthesis, benzyl chloride is used to introduce the benzyl protecting group in reaction with alcohols, yielding the corresponding benzyl ether, carboxylic acids, and benzyl ester. Benzoic acid (C 6 H 5 ...
In organic chemistry, the Menshutkin reaction converts a tertiary amine into a quaternary ammonium salt by reaction with an alkyl halide. Similar reactions occur when tertiary phosphines are treated with alkyl halides. Menshutkin-reaction. The reaction is the method of choice for the preparation of quaternary ammonium salts. [1]
However, if an unreactive alkylating agent is used (e.g. an alkyl chloride) then the rate of reaction can be greatly improved by the addition of a catalytic quantity of a soluble iodide salt (which undergoes halide exchange with the chloride to yield a much more reactive iodide, a variant of the Finkelstein reaction).
Benzoic acid is cheap and readily available, so the laboratory synthesis of benzoic acid is mainly practiced for its pedagogical value. It is a common undergraduate preparation. Benzoic acid can be purified by recrystallization from water because of its high solubility in hot water and poor solubility in cold water.
In IUPAC nomenclature, the prefix benzyl refers to a C 6 H 5 CH 2 substituent, for example benzyl chloride or benzyl benzoate. Benzyl is not to be confused with phenyl with the formula C 6 H 5 . The term benzylic is used to describe the position of the first carbon bonded to a benzene or other aromatic ring.
The benzyl alcohol thus formed is quickly converted to the chloride under the reaction conditions. Mechanism of Blanc chloromethylation Other possibilities for the electrophile include (chloromethyl)oxonium cation (ClH 2 C–OH 2 + ) or chlorocarbenium cation (ClCH 2 + ), which may be formed in the presence of zinc chloride. [ 4 ]
synthesis of benzamide from benzoyl chloride and a phenethylamine; synthesis of flutamide, a nonsteroidal antiandrogen; acylation of a benzylamine with acetyl chloride (acetic anhydride is an alternative) In the Fischer peptide synthesis (Emil Fischer, 1903), [6] an α-chloro acid chloride is condensed with the ester of an amino acid.
Together with the benzyltriethylammonium salt, benzyltrimethylammonium hydroxide is a popular phase-transfer catalyst. [2] It is used in aldol condensation reactions and base-catalyzed dehydration reactions. It is also used as a base in Ando's Z-selective variant of Horner-Wadsworth-Emmons Olefination reactions. [3]