Synthesis of cyclohexyl ethyl ether

Preparation of cyclohexyl ethyl ether

Alternative Names: ethoxycyclohexane; ethoxy-cyclohexane; cyclohexane, ethoxy-

Cyclohexyl ethyl ether is prepared by treating cyclohexanol with sodium and the obtained sodium cyclohexanolate with ethyl iodide. Due to the slow reaction between cyclohexanol with sodium best results are obtained when a ” molecular” (granulated) sodium is employed.

Preparation of cyclohexyl ethyl ether (ethoxycyclohexane; ethoxy-cyclohexane; cyclohexane, ethoxy-)

Preparation of cyclohexyl ethyl ether (ethoxycyclohexane; ethoxy-cyclohexane; cyclohexane, ethoxy-)

A “molecular” sodium (granulated sodium) is conveniently prepared from the powdered sodium in the flask in which the subsequent reaction is to be carried out. Into a 1-litre three-necked flask fitted with a reflux condenser (protected by a drying tube containing soda lime), a sealed stirrer and a dropping funnel, are placed 23 g of clean sodium and 150-200 ml of anhydrous xylene. The flask is surrounded by an oil bath, which is heated until the sodium has melted. The stirrer is started and after the sodium is suitably granulated, the oil bath is removed. When the contents of the flask have cooled to the room temperature, the stirrer is stopped. The xylene may then be decanted, and the sodium washed with two 100 ml portions of anhydrous ether to remove traces of xylene.  15.5 g of “molecular” sodium (granulated sodium) are prepared by described method under xylene and the xylene is replaced completely by 100 ml of anhydrous ether. An efficient reflux condenser is attached to the flask and slowly, with stirring, a solution of 66 g of pure cyclohexanol in 50 ml of anhydrous ether is dropwise added. The reaction mixture is left overnight to complete the formation of the sodium cyclohexanolate. 56 ml (108 g) of ethyl iodide are dropwise added while stirring so that the ether boils gently. The reaction is allowed to proceed for 12-18 hours, forming  a blue solid. A bent tube (to act as a still head) and a condenser are connected to the flask, and the reaction mixture is distilled in order to remove the diethyl ether. Then the distillation is continued as long as liquid passes over. The distillate (containing some unchanged cyclohexanol) is refluxed with a large excess of sodium and distilled again. Finally, the mixture is distilled over a little sodium, collecting the cyclohexyl ethyl ether at 148-150° C. The yield is 21 g. If the sodium is appreciably attacked, the distillation from a fresh quantity of sodium is repeated.

A text book of practical organic chemistry, by A. I. Vogel, 314-315, 1974

IUPAC Name

ethoxycyclohexane

InChI

InChI=1S/C8H16O/c1-2-9-8-6-4-3-5-7-8/h8H,2-7H2,1H3

InChI Key

GJJASJCGLOUWAC-UHFFFAOYSA-N

Canonical SMILES

CCOC1CCCCC1

Depositor-Supplied Synonyms

Ethoxycyclohexane, Cyclohexyl ethyl ether, ethoxy-cyclohexane, Cyclohexane, ethoxy-, AC1LBJKK, Cyclohexyl ethyl ether #, AC1Q58MA, SCHEMBL60435, GJJASJCGLOUWAC-UHFFFAOYSA-N, AR-1I7822, AKOS015906345, A844509, I14-21382

Removed Synonyms

CID559068, 932-92-3, 94204-74-7

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