Synthesis of cyclohexyl chloride

Preparation of cyclohexyl chloride

Alternative Names: chlorocyclohexane; cyclohexane, chloro-

Preparation of cyclohexyl chloride (chlorocyclohexane; cyclohexane, chloro-)

Preparation of cyclohexyl chloride (chlorocyclohexane; cyclohexane, chloro-)

In a 2000 ml round-bottomed flask, fitted with a reflux condenser, 100 grams of pure cyclohexanol, 250 ml of concentrated hydrochloric acid and 80 g of anhydrous calcium chloride are placed. The reaction mixture is heated on a boiling water bath for 10 hours with occasional shaking. The refluxing period may be reduced to 6 hours and the yield improved slightly by mechanical stirring. When the reaction is complete the flask is cooled the upper layer is separated, washed with saturated sodium chloride solution, saturated sodium bicarbonate solution, saturated sodium chloride solution, and dried the crude cyclohexyl chloride with excess of anhydrous calcium chloride for at least 24 hours. The crude cyclohexyl chloride is purified by fractional distillation. The fraction boiling at 141.5-142.5° C is collected yielding 90 grams of pure cyclohexyl chloride.

An alternative method of conducting the preparation of cyclohexyl chloride consists in treating 100 grams of cyclohexanol with 250 ml of concentrated hydrochloric acid, refluxing slowly whilst a stream of hydrogen chloride gas is passed into the mechanically stirred mixture for 3 hours. The cyclohexyl chloride, b.p. 141-143° C, is isolated as above yielding is 80 grams of final product.

A text book of practical organic chemistry, by A. I. Vogel, 275, 1974

Preparation of cyclohexyl chloride

Preparation of cyclohexyl chloride

To prepare the cyclohexyl chloride a molar ratio of cyclohexane 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 cyclohexane 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 60% of  cyclohexyl chloride, b.p. 67°C/62mm; n20/D 1.4626.

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

IUPAC Name

chlorocyclohexane

InChI

InChI=1S/C6H11Cl/c7-6-4-2-1-3-5-6/h6H,1-5H2

InChI Key

UNFUYWDGSFDHCW-UHFFFAOYSA-N

Canonical SMILES

C1CCC(CC1)Cl

Depositor-Supplied Synonyms

CHLOROCYCLOHEXANE, Cyclohexyl chloride, Cyclohexane, chloro-, 542-18-7, Monochlorocyclohexane, HSDB 2801, UNFUYWDGSFDHCW-UHFFFAOYSA-N, NSC 8434, EINECS 208-806-6, BRN 1900796, AI3-23841, Chlorcyclohexan, Chlorzyklohexan, chlor-cyclohexane, cyclohexylchloride, chloro-cyclohexane, chloranylcyclohexane, AC1L1WAW, ACMC-20aj27, UNII-PNV8C821FH, PNV8C821FH, SCHEMBL22803, KSC272C1T, C105058_ALDRICH, AC1Q3P72, 24160_FLUKA, CHEBI:39156, CTK1H2119, NSC8434, MolPort-001-783-746, LTBB002436, NSC-8434, ANW-75629, STL280356, AKOS005207255, AM90219, MCULE-9519865350, RP19325, AN-21344, CJ-05539, CJ-25292, KB-76053, LS-56754, S716, DB-021196, TR-019171, FT-0624210, 107283-EP2277898A2, 107283-EP2289965A1, 107283-EP2298766A1, 107283-EP2298828A1, 4-05-00-00048 (Beilstein Handbook Reference), A830041, 3B4-1004, I14-5922, I14-20924, InChI=1/C6H11Cl/c7-6-4-2-1-3-5-6/h6H,1-5H

Removed Synonyms

CID10952, c0153

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