Nitro benzyl chloride

The most valuable and comprehensive kinetic studies of alkylation have been carried out by Brown et al. The first of these studies concerned benzylation of aromatics with 3,4-dichloro- and 4-nitro-benzyl chlorides (these being chosen to give convenient reaction rates) with catalysis by aluminium chloride in nitrobenzene solvent340. Reactions were complicated by dialkylation which was especially troublesome at low aromatic concentrations, but it proved possible to obtain approximately third-order kinetics, the process being first-order in halide and catalyst and roughly first-order in aromatic this is shown by the data relating to alkylation of benzene given in Table 77, where the first-order rate coefficients k1 are calculated with respect to the concentration of alkyl chloride and the second-order coefficients k2 are calculated with respect to the products of the... 

The 2-hydroxy-5-nitrobenzyl chloride begins to separate as a solid about one hour after the beginning of the reaction. At the end the mixture is cooled in ice for one hour whereby more crystals separate, after which the acid liquors are either filtered or decanted from the crystals (Note 6). The 2-hydroxy-s-nitro-benzyl chloride is purified by recrystallization from 125 cc. of hot benzene (Note 7). The yield is 46 g. (69 per cent of the theoretical amount based on />-nitrophenol) of a white product melting at 129-130°. 

Dinitrobibenzyl has been prepared by the nitration of bibenzyl 2 by the action of alkaline zinc chloride on >-nitro-benzyl chloride 3 by the action of alkali on />-nitrotoluene 4 by the oxidation of a,a-bis( >-nitrobenzyl)hydrazine with mercuric oxide 6 and by the present method. ... 

Chloro 6 nitro benzoic acid acifluorfen, bifenox, fluoroglycifen, fomesafen 2 Chloro 5 nitro benzyl chloride flupoxam... 

Typical examples of this are found among the nitro derivatives of the benzene halides o-nitro benzyl chloride has a much more powerful lachr5miatory action than benzyl chloride or than the corresponding bromide or iodide. 

The radicles which react most easily are the NOj— group in 0- nitro benzyl chloride and bromide, the CO— group in the... 

According to Lindemann, it was used by the French during the war mixed with />-nitro benzyl chloride under the name of " Cedenite"... 

The reaction between 2-hydroxy-5-nitro-benzyl chloride with diethylamine yields 2-hydroxy-5-nitro-N, N, diethyl benzyl amine, which on reduction gives 5-amino-2-diethylamino ethyl phenol. 

Bromobenzene, iodobenzene and benzyl chloride behave somewhat similarly. The />-nitro-derivatives of the first two compounds frequently crystallise out even before pouring into water p-nitrobenzyl chloride usually remains as an oil for several minutes before solidifying. 

The p-chloro analog of phentermine has much the same activity as the parent compound, with perhaps a somewhat decreased activity on the central nervous system. Alkylation of p-chloro-benzyl chloride with the carbanion obtained from treatment of 2-nitropropane with strong base affords the compound containing the required carbon skeleton (74). Catalytic reduction of the nitro group yields chlorphentermine (75). ... 

As an alternative to radical chlorination, use has been made of carbon tetrachloride and hexachloroethane in the presence of a quaternary ammonium salt, as source of the chloronium ion for reaction with activated alkylbenzenes [38], Benzyl chlorides need the additional activation of a nitro group for their conversion into the corresponding nitrobenzotrichlorides, whereas benzal chlorides do not need the extra activation for a similar conversion. The same synthetic protocol, using hexachloroethane, has been used for the conversion of allylic sulphones into the 1,1-dichloro derivatives [39],... 

The facile homogeneous catalysed reduction of acid chlorides to alcohols has many advantages over reduction with sodium borohydride in hydroxylic solvents where rapid reaction of the acid chloride with the solvent can occur [10]. The procedure has been incorporated into a simple one-pot conversion of aroyl chlorides into the corresponding benzyl chlorides (Scheme 11.1) under liquidrliquid or solid-liquid two-phase conditions [11], The reduction of a limited number of aryl compounds was reported with ca. 70% overall yields, although poorer yields result from the reduction of 4-nitro-, 2-cyano- and 2,4-dichlorobenzoyl chlorides, and the reduction failed completely with terphthaloyl chloride and with its 2,3,5,6-tetrafluoro derivative [11]. 

Barek et al. have reported on the determination of AT-nitroso compounds, azo compounds, heterocychcs, aromatic nitro compounds, heterocychc amines and even benzyl chloride using electrochemical methods such as voltammetry and polarog-raphy. The nitro and AT-nitroso compounds work particularly well in reductive mode [47, 48]. For appropriate analytes, adsorptive stripping voltammetry and anodic stripping voltammetry can give orders of magnitude lower detection hmits than are available from HPLC with electrochemical detection [48]. 

Amino-PAHs, nitro-PAHs, A-nitroso cpds, azo cpds, benzyl chloride Metabolism, environmental analysis Polarography and voltammetry Review [48]... 

A still different scheme is used for the preparation of the benzimidazole buterizine (74). Alkylation of benzhydrylpiperazine with substituted benzyl chloride 70 gives the intermediate 7U Nucleophilic aromatic displacement on this compound by means of ethyl amine leads to reduction of the nitro group then gives the diamine T. Treatment of that with the orthoformate ester of pentanoic acid serves to form the imidazole ring. There is thus obtained the peripheral vasodilating agent buteri zi ne (74). ... 

Benzyl salicylate can be prepared by the reaction of benzyl chloride with an alkali salt of salicylic acid at 130—140°C or by the transesterification of methyl salicylate with benzyl alcohol. It is used as a fixative and solvent for nitro musks and as a fragrance for deteigents. Benzyl salicylate was priced at... 

Other syrupy, benzylated bromides bearing O-acetyl or O-p-nitro-benzoyl groups were also prepared and characterized,86-84 as well as a partially benzylated chloride.85 Acid hydrolysis of 22 gave crystalline 2-O-benzyl-a-L-fucose, which was acylated with p-nitrobenzoyl chloride-pyridine. Treatment84 of the resulting tris(p-nitrobenzoate) with hydrogen bromide-dichloromethane led to precipitation of p-nitrobenzoic acid and formation of syrupy 2-0-benzyl-3,4-di-0-(p-nitro-benzoyl)-a-L-fucopyranosyl bromide (33). 

Alkyl halides with an electron-withdrawing group on the halogen-bearing carbon can be dimerized to olefins by treatment with bases. Z may be nitro, aryl, etc. It is likely that in most cases the mechanism451 involves nucleophilic substitution followed by elimination452 (illustrated for benzyl chloride) ... 

Benzyl chloride and potassium selenocyanate give benzyl selenocyanate, which yields a para-compound on nitration, the latter also being obtained by the condensation of p-nitrobenzyl chloride with potassium selenocyanate. The strength of the nitric acid and the conditions of the nitration determine the resulting products in the case of chlorophenyl and tolyl compounds. Nitric acid (density 1 4) at 8° C. converts p-tolyl selenocyanate into di-2-nitro-p-tolyl diselenide and 2-nitro-p-tolylselenimc acid, whereas acid of density 1 5 at -10° C. yields 2-nitro-p-tolyl selenocyanate and a small amount of 3-nitro-p-tolyl selenocyanate. 

While interacting with the anion of 2-nitropropane, benzyl chloride and its derivatives bearing groups CN, CF3, Me2N+, Me, and Br in the para position yield products of O-alkylation (route a in Scheme 4-11). Meanwhile, when the nitro group occupies the para position instead of these substituents, the reaction gives the products of C-alkylation (route... 

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