Synthesis of 2-chlorotoluene

Preparation of 2-chlorotoluene (1-chloro-2-methylbenzene; o-chlorotoluene)

Preparation of 2-chlorotoluene (1-chloro-2-methylbenzene; o-chlorotoluene)

Preparation of 2-chlorotoluene (1-chloro-2-methylbenzene; o-chlorotoluene)

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.

Experiments in Organic Chemistry, L. F. Fieser, 216, 1941





InChI Key


Canonical SMILES


MeSH Synonyms

2-chlorotoluene, 2-chlorotoluene, ion(+1), o-chlorotoluene, ortho-chlorotoluene

Depositor-Supplied Synonyms

2-Chlorotoluene, 1-Chloro-2-methylbenzene, o-Chlorotoluene, 95-49-8, Benzene, 1-chloro-2-methyl-, Toluene, o-chloro-, o-Tolyl chloride, ortho-Chlorotoluene, 2-Chloro-1-methylbenzene, 2-Methylchlorobenzene, Halso 99, 1-METHYL-2-CHLOROBENZENE, NSC 8766, UNII-2G7D0YDV9H, 1-chloro-2-methyl-benzene, 2G7D0YDV9H, CCRIS 7785, HSDB 5291, IBSQPLPBRSHTTG-UHFFFAOYSA-N, EINECS 202-424-3, BRN 1904175, AI3-15912, DSSTox_CID_3977, DSSTox_RID_77246, DSSTox_GSID_23977, CAS-95-49-8, o-tolylchloride, Monochlorotoluene, 2 -chlorotoluene, ortho-tolyl chloride, PubChem19748, AC1L1OBG, TOLUENE,2-CHLORO, ACMC-209rz3, SCHEMBL12792, KSC486M8P, 47797_SUPELCO, 111910_ALDRICH, 36695_RIEDEL, CHEMBL1797265, SCHEMBL10738408, 26530_FLUKA, 36695_FLUKA, CTK3I6687, NSC8766, MolPort-001-768-903, LTBB002091, NSC-8766, Tox21_201251, Tox21_300329, ANW-40525, STL280355, ZINC01648221, AKOS000120015, LS11417, MCULE-2832835864, MP-2125, RL06013, RTR-029801, NCGC00247992-01, NCGC00247992-02, NCGC00254384-01, NCGC00258803-01, AJ-28724, AK109120, AN-24320, CJ-05924, CJ-26625, KB-68560, LS-154030, ST2408745, TR-029801, FT-0612029, FT-0651834, S0659, EC 202-424-3, o-Chlorotoluene [UN2238] [Flammable liquid], o-Chlorotoluene [UN2238] [Flammable liquid], 4-05-00-00805 (Beilstein Handbook Reference), 3B4-0431, S01-0312, InChI=1/C7H7Cl/c1-6-4-2-3-5-7(6)8/h2-5H,1H

Removed Synonyms

o-Toluyl chloride, CHLOROTOLUENE, UN 2238 (Related), CID7238, UN2238, c0295, 3-methyl-1,2,4,7,8,9,10,10a-octahydropyrido[1,2-d][1,4]diazepin-5-one

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