Synthesis of 1-chloro-2-(dichloromethyl)benzene

Preparation of 1-chloro-2-(dichloromethyl)benzene

Preparation of 1-chloro-2-(dichloromethyl)benzene

Preparation of 1-chloro-2-(dichloromethyl)benzene

Chlorination apparatus consists of a round-bottom 500 ml three-necked flask equipped with a reflux condenser, a thermometer and a tube extending to the bottom for introducing chlorine. To the flask 254 g (2 mol) of o-chlorotoluene containing no iron (iron is a catalyst for directing the chlorine in the benzene ring. Moreover, the catalytic action of iron facilitates the condensation of 1-chloro-2-(dichloromethyl)benzene hydrogen chloride and the formation of tar products.), and 2 g of phosphorus trichloride are placed. The flask is weighed on scales and placed near a window in bright sunlight or by illuminating the reaction with the mercury lamp. The top of  reflux condenser is further connected to absorption flask for hydrogen chloride. The flask is heated to a temperature of 130° C and chlorine starts to pass. As the chlorination reaction temperature gradually rises, reaching 160-170° C, chlorination is carried out until the weight gain of the reaction mixture reached 136-137 g, and a specific gravity of liquid (at 20° C) 1.395-1.400. After addition of the chlorine gas is stopped reaction mixture is continued to boiled to remove an excess of hydrogen chloride and then cooled. The mixture was then vacuum distilled by using distillation column (diameter 25 mm, length 60 cm) connected to condenser and fraction receiver. 2-chlorobenzaldehyde is collected in the range 101.5- 130° C / 10 mm Hg yielding 300-310 g of a colorless liquid with a very pungent odor.

Препаративная органическая химия, Вульфсон Н.С., 195-196, 1959 (Preparative organic chemistry, Wolfson N. S., 195-196, 1959)

IUPAC Name

1-chloro-2-(dichloromethyl)benzene

InChI

InChI=1S/C7H5Cl3/c8-6-4-2-1-3-5(6)7(9)10/h1-4,7H

InChI Key

BXSVYGKOUULJCL-UHFFFAOYSA-N

Canonical SMILES

C1=CC=C(C(=C1)C(Cl)Cl)Cl

Depositor-Supplied Synonyms

Chloro(dichloromethyl)benzene, 1-Chloro-2-(dichloromethyl)benzene, alpha,alpha,ar-Trichlorotoluene, 88-66-4, Benzene, chloro(dichloromethyl)-, Toluene, alpha,alpha,ar-trichloro-, Benzene, 1-chloro-2-(dichloromethyl)-, 2-chlorobenza1 chloride, AC1L25SB, SCHEMBL947512, CTK5G1164, BXSVYGKOUULJCL-UHFFFAOYSA-N, EINECS 201-849-1, AKOS006273196, Benzene,1-chloro-2-(dichloromethyl)-, LS-29470, 98715-38-9

Removed Synonyms

1-Chloro-2- benzene, CID66624

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