Synthesis of (2-chloroethyl)benzene

Preparation of (2-chloroethyl)benzene

Preparation of (2-chloroethyl)benzene

Preparation of (2-chloroethyl)benzene

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 ethylbenzene 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 b.p. 200°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 additional fractions are collected within narrower limits. The yield is 60%, b.p. 200°C; 82-84°C/16 mm; 77°C/15 mm; n20/D 1.53; 1.069 g/ml at 25 °C. In addition, 15-20% of (1-chloroethyl)benzene is produced (b.p. 195°C, 90 °C/33 mm, n20/D 1.526).

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

Synthesis of (2-chloroethyl)benzene

Synthesis of (2-chloroethyl)benzene

To prepare the (2-chloroethyl)benzene a molar ratio of ethylbenzene to sulfuryl chloride of 1.2:1 is used. After the addition of 0.002 mole of benzoyl peroxide or, still better, azo-bis-isobutyronitrile (referred to 1 mole of sulfuryl chloride) the ethylbenzene and the sulfuryl chloride are heated to the boil in a round-bottomed flask with a very efficient reflux condenser and a calcium chloride tube. At intervals of 1 hr, the same amount of chain initiator is added. The reaction is complete in 8-10 hours and  when no further evolution of gas can be observed. The mixture is allowed to cool and is washed with water and it is then dried with magnesium sulfate and fractionated through a 20-cm Vigreux column yielding 85% of (2-chloroethyl)benzene, b.p. 77°C/15mm; n20/D 1.5278. The (2-chloroethyl)benzene obtained by described method contains a little l-phenyl-2-chloroethane.

Organicum. Practical Handbook of Organic Chemistry, by Heinz Becker, Werner Berger and Günter Domschke, Addison-Wesley Pub. Co, 170, (1973)

IUPAC Name

2-chloroethylbenzene

InChI

InChI=1S/C8H9Cl/c9-7-6-8-4-2-1-3-5-8/h1-5H,6-7H2

InChI Key

MNNZINNZIQVULG-UHFFFAOYSA-N

Canonical SMILES

C1=CC=C(C=C1)CCCl

Depositor-Supplied Synonyms

(2-Chloroethyl)benzene, Phenethyl chloride, 622-24-2, 2-Phenylethyl chloride, Benzene, (2-chloroethyl)-, Phenethylchloride, 1-Chloro-2-phenylethane, 2-chloroethylbenzene, 2-Phenyl-1-chloroethane, .beta.-Phenethyl chloride, Ethylchlorobenzene, 2-Chloroethyl Benzene, alpha-Chloroethylbenzene, beta-Phenylethyl chloride, .beta.-Phenylethyl chloride, (.beta.-Chloroethyl)benzene, BENZENE, CHLOROETHYL-, MNNZINNZIQVULG-UHFFFAOYSA-N, NSC 27886, 1331-31-3, chloroethylbenzene, phenyl ethyl chloride, 2-chloro ethylbenzene, 2-chloro ethyl benzene, (2-chloroethyl)-benzene, PHENYLETHYLCHLORIDE, AC1L5LTJ, AC1Q3UIS, (beta-Chloroethyl)benzene, ACMC-1BC5M, (2-chloro-ethyl)-benzene, UNII-C7T86VN1QZ, C7T86VN1QZ, C40405_ALDRICH, KSC163A5R, SCHEMBL124719, SCHEMBL5705619, MolPort-001-785-836, BB_SC-4527, NSC27886, ZINC1641679, EINECS 210-725-6, ANW-34110, BBL027318, NSC-27886, SBB070687, STK802209, ZINC01641679, AKOS000120652, AS00650, MCULE-8511172459, AJ-28640, AK-59791, CJ-26506, KB-79912, LS-29489, OR019919, OR214074, SC-16071, AB0007054, DB-054098, KB-229285, KB-230170, KB-283507, RT-001375, ST2414175, TL8004067, W7426, X-4309, I01-6853, W-105031, 3B3-036096, InChI=1/C8H9Cl/c9-7-6-8-4-2-1-3-5-8/h1-5H,6-7H

Removed Synonyms

m-Chloroethylbenzene, p-Chloroethylbenzene, 1-Chloro-1-phenylethane, beta-Phenethyl chloride, C8H9Cl, O-CHLOROETHYLBENZENE, c0167, CID231496, CEE

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