Synthesis of 1-ethoxyhexane

Preparation of 1-ethoxyhexane

Preparation of 1-ethoxyhexane

Preparation of 1-ethoxyhexane

To prepare 1-ethoxyhexane (n-hexyl ethyl ether), an alkoxide solution is first prepared from 0.25 gramequivalent of metallic sodium and 1.2 mole of the absolute n-hexyl alcohol in a three-necked flask provided with a stirrer and reflux condenser. To the obtained alkoxide is added 0.2 mole of ethyl iodide (alternatively ethyl bromide), and the mixture is heated under reflux with stirring and exclusion of moisture for 5 hours. The yield of 1-ethoxyhexane is 80%, n20/D 1.4008; b.p. 142°C. The reaction product is distilled off directly with stirring until the boiling point of the n-hexyl alcohol used is reached (156°C). The distillate, which consists of ether and the alcohol used, is fractionated into narrower fractions through a 30-cm Vigreux column. Several fractions are collected, the refractive index of each of which must be determined. The fractions consisting essentially of the desired ether are combined and are distilled over 5% of sodium repeatedly until the given refractive index is reached.

Organicum. Practical Handbook of Organic Chemistry, by Heinz Becker, Werner Berger and Günter Domschke, Addison-Wesley Pub. Co, 208-210, (1973)

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

1-Ethoxyhexane, Ether, ethyl hexyl, Hexane, 1-ethoxy-, 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, Alcohols, C6-12, ethoxylated, CTK5A7072, ZXHQLEQLZPJIFG-UHFFFAOYSA-N, AKOS006286626, (C6-C10) Alkyl alcohol, ethoxylated, AS02559, LP004063, LS-191717, 337520-86-2

Removed Synonyms

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

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