Synthesis of 2-methylbenzyl chloride

Preparation of 2-methylbenzyl chloride

The chlorination is best carried out in a three-necked flask with a mercury immersion lamp, a gas inlet tube, and a highly efficient reflux condenser.

A glass apparatus for the photochlorination

A glass apparatus for the photochlorination

If no mercury immersion lamp is available, the mixture can be irradiated from outside with a 500-watt photolamp or the chlorination can be carried out in direct sunlight. However, the reaction then takes place somewhat more slowly and the yields are generally lower. The gaseous chlorine is dried in a wash-bottle with concentrated sulfuric acid. An empty wash-bottle must be connected on either side of this washing bottle as safety vessels. The o-xylene is heated to the boiling point, using a heating bath, and a vigorous stream of gaseous chlorine is passed in. During the chlorination reaction no gaseous chlorine should pass through the condenser (color). Chlorination is continued until the calculated increase in weight has been obtained or until the vigorously boiling contents of the flask have reached an empirically determined temperature (in the liquid 175 °C). The reaction product is fractionated through a 20-cm Vigreux column in vacuum after the addition of small amount of sodium hydrogen carbonate. In order to obtain pure product, the main fraction first obtained is fractionated again, and fractions are collected within narrower limits. The yield is 70% b.p. 197-199 °C; b.p. 91°C/18 mm; nD/1.5387;

Organicum. Practical Handbook of Organic Chemistry, by Heinz Becker, Werner Berger and Günter Domschke, Addison-Wesley Pub. Co, 168-169,  (1973)

IUPAC Name

1-(chloromethyl)-2-methylbenzene

InChI

InChI=1S/C8H9Cl/c1-7-4-2-3-5-8(7)6-9/h2-5H,6H2,1H3

InChI Key

VQRBXYBBGHOGFT-UHFFFAOYSA-N

Canonical SMILES

CC1=CC=CC=C1CCl

Depositor-Supplied Synonyms

2-Methylbenzyl chloride, 1-(Chloromethyl)-2-methylbenzene, 552-45-4, o-Xylyl chloride, ALPHA-CHLORO-O-XYLENE, o-Methylbenzyl chloride, Benzene, 1-(chloromethyl)-2-methyl-, o-(Chloromethyl)toluene, 2-Methylbenzylchloride, 2-(Chloromethyl)toluene, o-Xylene, .alpha.-chloro-, 1-Chloromethyl-2-methyl-benzene, VQRBXYBBGHOGFT-UHFFFAOYSA-N, 1-(Chloromethyl)-2-Methyl-Benzene, omega-Chloro-o-xylene, PubChem7487, o-Xylyl-alpha-chloride, 2-methyl-benzyl chloride, AC1L1WLN, .alpha.-Chloro-o-xylene, .omega.-Chloro-o-xylene, o-Xylene, alpha-chloro-, o-Xylyl-.alpha.-chloride, ACMC-1AQ0Z, UNII-EQT3V044TW, .alpha.-Chloro-ortho-xylene, DSSTox_CID_24441, DSSTox_RID_80231, EQT3V044TW, DSSTox_GSID_44441, SCHEMBL52225, C73303_ALDRICH, KSC193E0N, 1-Chloromethyl-2-methylbenzene, Benzene, (chloromethyl)methyl-, AC1Q2F23, AC1Q2R13, CHEMBL3183322, CTK0J3206, HSDB 2681, MolPort-000-871-660, BB_SC-7008, ZINC2034794, EINECS 209-013-8, Tox21_302160, ANW-32272, BBL009703, SBB040606, STL141068, ZINC02034794, AKOS000121523, AS03843, MCULE-2014896403, TRA0099462, NCGC00255750-01, AJ-33012, AK-53468, AM100941, AN-45846, CAS-552-45-4, CJ-31934, KB-11971, KB-86064, OR011043, OR119425, OR237172, SC-76845, DB-000160, METHYL, [2-(CHLOROMETHYL)PHENYL]-, RT-000937, ST2415081, FT-0632374, A26507, I01-5869, 3B3-036338, 1-(Chloromethyl)-2-methyl-benzen;2-(Chloromethyl)toluene, InChI=1/C8H9Cl/c1-7-4-2-3-5-8(7)6-9/h2-5H,6H2,1H, 26519-66-4, 99765-61-4

Removed Synonyms

|A-chloro-o-xylene, C8H9Cl, CID11093, c0864, H0845

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