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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 ...
Like most alcohols, it reacts with carboxylic acids to form esters. In organic synthesis, benzyl esters are popular protecting groups because they can be removed by mild hydrogenolysis. [6] Benzyl alcohol reacts with acrylonitrile to give N-benzylacrylamide. This is an example of a Ritter reaction: [7] C 6 H 5 CH 2 OH + NCCHCH 2 → C 6 H 5 CH ...
Benzyl is commonly used in organic synthesis as a robust protecting group for alcohols and carboxylic acids. Treatment of alcohol with a strong base such as powdered potassium hydroxide or sodium hydride and benzyl halide (BnCl or BnBr) [9] [10]
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]
[70] [71] Can be formed from diazomethane in diethyl ether, [72] [73] [74] caesium carbonate and methyl iodide in N,N‑dimethylformamide, [75] or methanol and catalytic trimethylsilyl chloride [76] Benzyl esters — Also removed by hydrogenolysis. [77] Benzhydryl esters — Same as benzyl, but easier to cleave [78]
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]
Benzyl chloroformate is commonly used in organic synthesis for the introduction of the benzyloxycarbonyl (formerly called carboxybenzyl) protecting group for amines.The protecting group is abbreviated Cbz or Z (in honor of discoverer Zervas), hence the alternative shorthand designation for benzyl chloroformate as Cbz-Cl or Z-Cl.
For example, when carried out in the presence of tert-butanol, the reaction generates Boc-protected amines, useful intermediates in organic synthesis. [24] [25] Likewise, when the Curtius reaction is performed in the presence of benzyl alcohol, Cbz-protected amines are formed. [26]