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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]
As is typical for an S N 2 process, benzylic, allylic, and α-carbonylated alkyl halides are excellent reactants. Even though alkyl chlorides are poor alkylating agents ( gem -dichlorides especially so), amines should not be handled in chlorinated solvents such as dichloromethane and dichloroethane, especially at high temperatures, due to the ...
Benzylamine is used as a masked source of ammonia, since after N-alkylation, the benzyl group can be removed by hydrogenolysis: [10] C 6 H 5 CH 2 NH 2 + 2 RBr → C 6 H 5 CH 2 NR 2 + 2 HBr C 6 H 5 CH 2 NR 2 + H 2 → C 6 H 5 CH 3 + R 2 NH. Typically a base is employed in the first step to absorb the HBr (or related acid for other kinds of ...
Benzyl chloride is prepared industrially by the gas-phase photochemical reaction of toluene with chlorine: [3]. C 6 H 5 CH 3 + Cl 2 → C 6 H 5 CH 2 Cl + HCl. In this way, approximately 100,000 tonnes are produced annually.
Chemically, phenyethanolamine is an aromatic compound, an amine, and an alcohol. The amino-group makes this compound a weak base , capable of reacting with acids to form salts. Two common salts of phenylethanolamine are the hydrochloride, C 8 H 11 NO.HCl, m.p. 212 °C, [ 6 ] and the sulfate, (C 8 H 11 NO) 2 .H 2 SO 4 , m.p. 239–240 °C.
The name "Schotten–Baumann reaction conditions" often indicate the use of a two-phase solvent system, consisting of water and an organic solvent. The base within the water phase neutralizes the acid, generated in the reaction, while the starting materials and product remain in the organic phase, often dichloromethane or diethyl ether .
Benzyl chloride can also be converted via benzyl cyanide with subsequent hydrolysis into phenylacetic acid. [ 22 ] [ 23 ] The disubstituted benzal chloride is converted to benzaldehyde , a popular flavorant [ 24 ] and intermediate for the production of malachite green and other dyes. [ 25 ]
One workaround to avoid this method is to reduce the carboxylic acid derivative all the way down to an alcohol, then oxidize the alcohol back to an aldehyde. Other alternatives include forming a thioester or a Weinreb amide, then reducing the new species to an aldehyde through the Fukuyama reduction or Weinreb reaction respectively, or using ...