Synthesis of ethyl hexyl ether

Preparation of ethyl hexyl ether (ether, ethyl hexyl; hexane, 1-ethoxy-; 1-ethoxyhexane; 1-ethoxy-hexane)

A 500-ml two neck round bottom is fitted with a reflux condenser and a dropping funnel. 249.5 ml (204 g) of dry n-hexyl alcohol are placed and 5.75 g of clean sodium are added in small pieces. The mixture is warmed under reflux until all the sodium has reacted (~2 hours). 20 ml (39 g) of ethyl iodide are dropwise added from the dropping funnel (sodium iodide gradually separates) and the obtained mixture is refluxed gently for 2 hours. The apparatus is rearranged for distillation and the crude ether is collected at 143-148° C (27 g). When cold, the apparatus is rearranged as previously with a dropping funnel and a reflux condenser. A further 5.75 g of clean sodium are added and the mixture is warmed until all sodium has reacted (alternatively, the reaction is left to proceed overnight, by which time all the sodium will react). A further 20 ml (39 g) of ethyl iodide are introduced and the mixture is reflux for 2 hours. The apparatus is rearranged for distillation and the crude ether is collected at 143-148° C. The two distillates are combined, the crude ether is removed from n-hexyl alcohol by heating under reflux for 2 hours with a large excess of sodium. A bent tube (to act as a still head) is attached to the flask and the mixture is distilled until no more liquid passes over. The resulting liquid is distilled from a few grams of sodium contained in a distillation flask fitted with fractionating column and the ethyl n-hexyl ether fraction boiling at 140-143° C is collected yielding 30 grams of final product. If the sodium is appreciably attacked, indicating that all the n-hexyl alcohol has not been completely removed, the distillation is repeated from a little fresh sodium.

A text book of practical organic chemistry, by A. I. Vogel, 313-314, 1974

IUPAC Name

1-ethoxyhexane

InChI

InChI=1S/C8H18O/c1-3-5-6-7-8-9-4-2/h3-8H2,1-2H3

InChI Key

ZXHQLEQLZPJIFG-UHFFFAOYSA-N

Canonical SMILES

CCCCCCOCC

MeSH Synonyms

ethyl hexyl ether

Depositor-Supplied Synonyms

Ether, ethyl hexyl, Hexane, 1-ethoxy-, 1-Ethoxyhexane, 5756-43-4, 70879-83-3, 1-ethoxy-hexane, Ethyl hexyl ether, 1-Ethoxyhexane #, ethyl n-hexyl ether, HEXYL ETHYL ETHER, AC1L3A8M, SCHEMBL127730, Alcohols, C6-1O, ethoxylated, Alcohols, C6-10, ethoxylated, CTK5A7072, ZXHQLEQLZPJIFG-UHFFFAOYSA-N, AKOS006286626, (C6-C10) Alkyl alcohol, ethoxylated, AS02559, LS-191717, 337520-86-2

Removed Synonyms

(Hydroxyethyloxy)tri(Ethyloxy)octane, CID111843, C8E

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