O Chlorotoluene

Method 1. Place 1250 ml. of water, 75 g, of pure potassium permanganate and 50 g. of o-chlorotoluene (Section IV,61) in a 2 -5-litre threenecked flask equipped with a mechanical stirrer and reflux condenser. 

Once the intermediacy of an aryne intermediate was established the reason for the observed regioselectivity of substitution mo m and p chlorotoluene became evident Only a single aryne intermediate may be formed from o chlorotoluene but this aryne yields a mixture containing comparable amounts of o and m methylanilme... 

Reactions of the Aromatic Ring. Ring chlorination of o-chlorotoluene yields a mixture of all four possible dichlorotoluenes, the 2,3-, 2,4-, 2,5-, and 2,6-isomers as shown in equation 1 (14). 

Halogen Reactions. Hydrolysis of chlorotoluenes to cresols has been effected by aqueous sodium hydroxide. Both displacement and benzyne formation are involved (27,28). o-Chlorotoluene reacts with sodium in Hquid ammonia to afford a mixture of 67% of o-toluidine [95-53-4] and 33% of yW-toluidine [108-44-1], C H CIN, as shown in equation 3 (29). 

Inhalation of high concentrations of monochlorotoluenes will cause symptoms of central nervous system depression. Inhalation studies produced an LC q (rat, 4 h) of 7119 ppm for o-chlorotoluene (68). o- and Chlorotoluene are both considered moderately toxic by ingestion (Table 2). A study of the relationship between the electronic stmcture and toxicity parameters for a series of mono-, di-, and tri-chlorotoluenes has been reviewed (72). A thin-layer chromatographic method has been developed to assess the degree of occupational exposure of workers to chlorotoluenes by determining j -cblorobippuric... 

Chlorotoluene isomer mixtures, especially those containing a relatively high amount of o-chlorotoluene, are widely used as solvents in industry for such purposes as metal-cleaning formulations, railroad industrial cleaners, diesel fuel additives, carbon removal procedures, paint thinners, and agricultural chemicals. Halso 99 andHalso 125 are examples of such solvents. 

Chloropropionitrile, 41 o-Chlorostyrene, 41 Chlorosulphonic acid, 41 Chlorothalonil, 41 o-Chlorotoluene, 41 Chloroxuron, 41... 

Arynes are intermediates in certain reactions of aromatic compounds, especially in some nucleophilic substitution reactions. They are generated by abstraction of atoms or atomic groups from adjacent positions in the nucleus and react as strong electrophiles and as dienophiles in fast addition reactions. An example of a reaction occurring via an aryne is the amination of o-chlorotoluene (1) with potassium amide in liquid ammonia. According to the mechanism given, the intermediate 3-methylbenzyne (2) is first formed and subsequent addition of ammonia to the triple bond yields o-amino-toluene (3) and m-aminotoluene (4). It was found that partial rearrangement of the ortho to the meta isomer actually occurs. 

However, this oxidation to carbonyl failed with the complexes of tetralin, o-chlorotoluene, 9,10-dihydrophenanthrene, and acenaphthalene [109]. The aniline complex can be oxidized to the nitrobenzene complex using H202 in CF3C02H [86] Eq. (38). This reaction parallels the analogous oxidation of aminocobaltici-nium [86, 111],... 

The results for the hydrolysis of chlorobenzene, o-chlorotoluene and p-chloroanisole in presence of cuprous oxide at different temperatures (Fig. 14) show a good selectivity for the reaction of the chlorobenzene. But, the p-chloroanisole is also transformed by a secondary demethylation reaction into the corresponding p-chlorophenolate. 

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