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ChemicalBook CAS DataBase List 2-Chlorotoluene
95-49-8

2-Chlorotoluene synthesis

12synthesis methods
The solution of cuprous chloride is cooled in an ice bath 0-5° C temperature. In this cold solution, the 2-methylbenzenediazonium is poured with constant shaking and allowing the mixture to come to room temperature. After about 10 minutes, the mixture gradually warmed with a good shaking.As the temperature rises the brown addition product begins to decompose with the evolution of nitrogen and with the formation of an oily layer of 2-chlorotoluene. When the decomposition reaction is at an end, the mixture is steam distilled, continuing the process only as long as oily droplets are present in the distillate, for the product is not appreciably soluble in water. The layer of 2-chlorotoluene is carefully separated and washed twice with an equal volume of concentrated sulfuric acid, which removes both the 2-cresol and the azo compound. Then 2-chlorotoluene is washed with water in order to remove the inorganic acid. Finally, 2-chlorotoluene is dried over calcium chloride, distilled, using an air condenser and collecting the product boiling at 153-158° C. Pure 2-chlorotoluene boils at 157° C. The yield is 25-30 g.
synthesis of 2-chlorotoluene
Experiments in Organic Chemistry, L. F. Fieser, 216, 1941
Highly Selective Oxidative Monochlorination To Synthesize Organic Intermediates: 2-Chlorotoluene, 2-Chloroaniline, 2-Chlorophenol, and 2-Chloro-4-methylphenol
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Yield:95-49-8 87%

Reaction Conditions:

Stage #1: o-toluidine hydrochloridewith isopentyl nitrite in acetone at 0 - 15;
Stage #2: with copper dichloride in ethanol;acetone at 5 - 20; for 2 h;Sandmeyer Reaction;Reagent/catalyst;Solvent;Temperature;

Steps:

1 Example 1

To a 100 ml three-necked flask was added 7.2 g of 2-methylaniline hydrochloride, 30 ml of acetone, and the ice-water bath was cooled to 0°C.8.8g of isoamyl nitrite was added dropwise, the temperature of the dropping process system was increased, the dropping rate was controlled, and the temperature was controlled at 0-15°C.Upon completion of the addition, 2-methylaniline hydrochloride dissolved and the system appeared pale yellow.5.0 g of copper chloride was dissolved in 30 ml of ethanol and added dropwise to the above system to control the dropping rate and the temperature was lower than 5°C.During the dropwise addition, yellow solids precipitated in the system, and the color deepened. The viscosity of the system became viscous with the addition of one third, and the reaction system was yellow-green with the dropwise addition of the copper chloride ethanol solution. After the addition was completed, the reaction was carried out in an ice bath for 20 minutes, gradually warmed to room temperature and reacted for 2 hours, and the system turned from yellow-green to dark green.Using 50ml of toluene, spin-degassing, precipitation of green solids, filtration, 5.0g; distillation,154-158°C distillate 5.5g was collected with a yield of 87%.

References:

CN107805180,2018,A Location in patent:Paragraph 0034-0038; 0042-0044

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