Synthesis of dihexyl ether

Preparation of dihexyl ether

Alternative Names: hexyl ether; n-hexyl ether; hexane, 1,1′-oxybis-; ether, dihexyl

Preparation of dihexyl ether (hexyl ether; n-hexyl ether; hexane, 1,1'-oxybis-; ether, dihexyl)

Preparation of dihexyl ether (hexyl ether; n-hexyl ether; hexane, 1,1′-oxybis-; ether, dihexyl)

For the preparation of dihexyl ether, the Dean-Stark apparatus is fitted with a round bottom flask and a condenser.

A glass apparatus for the preparation of dihexyl ether

A glass apparatus for the preparation of dihexyl ether

A small amount of water is placed in the Dean-Stark apparatus. A mixture of 61 ml (50 g) of n-hexyl alcohol and with 3.5 ml (6 g) of concentrated sulfuric acid are added in the round bottom flask. The flask is gently heated so that the liquid refluxes and is condensed by the condenser. Water and n-hexyl alcohol will first collect in the Dean-Stark apparatus, and when the combined volumes exceed certain volume (depending on Dean-Stark used), automatic separation of the two liquids will commence; the denser water will fall to the bottom of the tube and the lighter n-hexyl alcohol will pass back into the flask. The heating is continued for 90 minutes and the temperature inside the flask rises to 180° C. The reaction is complete when 5 ml of water is collected in Dean-Stark apparatus. When the reaction is complete the reaction mixture is poured into water, the upper layer is separated, washed with 5% sodium hydroxide solution, then with water and dried over anhydrous potassium carbonate. The dried product is filtered in into a distilling flask and purified by distillation. The fractions boiling at (I) 160-221° C (17 g), (II) 221-223° C (17 g) are collected. The fraction (I) is refluxed for 1 hour in a small flask with 3 g of sodium and distilled from the sodium hexan-1-olate and excess of sodium yielding fairly pure fraction (III) of dihexyl ether. The fractions (II) and (III) are combined and distilled from a little sodium. The fraction boiling at 221.5-223° C is collected yielding 19 grams pure n-hexyl ether.

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

IUPAC Name

1-hexoxyhexane

InChI

InChI=1S/C12H26O/c1-3-5-7-9-11-13-12-10-8-6-4-2/h3-12H2,1-2H3

InChI Key

BPIUIOXAFBGMNB-UHFFFAOYSA-N

Canonical SMILES

CCCCCCOCCCCCC

Depositor-Supplied Synonyms

Dihexyl ether, Hexyl ether, N-Hexyl ether, Hexane, 1,1′-oxybis-, 112-58-3, Ether, dihexyl, Bis(1-hexyl)ether, DI-N-HEXYL ETHER, 1-hexoxyhexane, 1-(Hexyloxy)hexane, Bis(1-hexyl) ether, 1,1′-Oxybis(hexane), hexyloxyhexane, BPIUIOXAFBGMNB-UHFFFAOYSA-N, NSC 9286, EINECS 203-987-8, SBB061195, BRN 1738177, AI3-01454, dihexylether, hexylether, n-Hexylether, Hexane,1′-oxybis-, Hexyl ether (8CI), 1-(Hexyloxy)hexane #, ACMC-1BXJM, AC1L1QHJ, AC1Q2WGV, SCHEMBL66247, 261505_ALDRICH, WLN: 6O6, CTK0H9734, NSC9286, MolPort-001-783-778, NSC-9286, ANW-16492, ZINC01699898, AKOS024390939, AN-22710, CJ-28643, LS-67824, DB-041100, RT-003555, FT-0625184, ST51047245, 4-01-00-01698 (Beilstein Handbook Reference), 3B3-023413, I14-112264, InChI=1/C12H26O/c1-3-5-7-9-11-13-12-10-8-6-4-2/h3-12H2,1-2H

Removed Synonyms

CID8198, H0138

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