Synthesis of cyclohexyl iodide

Preparation of cyclohexyl iodide

Alternative Names: iodocyclohexane; cyclohexyl iodide; cyclohexane, iodo-

Preparation of cyclohexyl iodide from cyclohexanol, orthophosphoric and potassium iodide

Preparation of cyclohexyl iodide from cyclohexanol, orthophosphoric and potassium iodide

Preparation of cyclohexyl iodide from cyclohexanol, orthophosphoric and potassium iodide

The orthophosphoric acid must be adjusted to a concentration of 95%. Alternatively, the commercial 100% orthophosphoric acid may be diluted with water to this concentration. Anhydrous orthophosphoric acid has limited solubility of hydrogen iodide and gives poorer yield.

In a 500 ml. three-necked flask, equipped with a thermometer, an air tight stirrer and a reflux condenser, 32.5 grams of phosphorus pentoxide and or 67.5 ml (or 115.5 grams) of 85% orthophosphoric acid. When the stirred mixture has cooled to room temperature, a mixture of 166 grams of potassium iodide and 50 grams of cyclohexanol (b.p. 160-161° C) are introduced. The mixture is heated with stirring at 100-120° C for 2-3 hours then  cooled the to room temperature and treated with the mixture of 75 ml of water and 125 ml of ether. The ethereal layer is separated, decolorized with 25 ml of 10% sodium thiosulfate solution, washed with 100 ml of cold, saturated sodium chloride solution, and dried with anhydrous magnesium sulfate. The ether is removed by evaporation and the crude cyclohexyl iodide is purified by distillation under diminished pressure. The fraction boiling at 67-69° C/9 mm is collected yielding 90 grams of pure cyclohexyl iodide.

A text book of practical organic chemistry, by A. I. Vogel, 284, 1974

IUPAC Name

iodocyclohexane

InChI

InChI=1S/C6H11I/c7-6-4-2-1-3-5-6/h6H,1-5H2

InChI Key

FUCOMWZKWIEKRK-UHFFFAOYSA-N

Canonical SMILES

C1CCC(CC1)I

Depositor-Supplied Synonyms

IODOCYCLOHEXANE, Cyclohexyl iodide, Cyclohexane, iodo-, 626-62-0, Cyclohexyliodide, FUCOMWZKWIEKRK-UHFFFAOYSA-N, iodo-cyclohexane, 1-iodocyclohexane, NSC6075, ACMC-1ATT4, AC1L1Z9O, c-C6H11I, SCHEMBL73820, 238244_ALDRICH, MolPort-001-781-548, NSC 6075, NSC-6075, EINECS 210-957-8, AKOS000118786, MCULE-4499971048, AK164074, BP-21170, CJ-28270, KB-77912, DB-054238, TC-166530, TL8004229, FT-0627261, I0056, I14-20993, 3B3-029062, InChI=1/C6H11I/c7-6-4-2-1-3-5-6/h6H,1-5H

Removed Synonyms

CID12289

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