Synthesis of diisoamyl ether

Preparation of diisoamyl ether (isoamyl ether; diisoamyl ether; isopentyl ether; diisopentyl ether; isoamyl oxide)

Preparation of diisoamyl ether (isoamyl ether; diisoamyl ether; isopentyl ether; diisopentyl ether; isoamyl oxide)

Preparation of diisoamyl ether (isoamyl ether; diisoamyl ether; isopentyl ether; diisopentyl ether; isoamyl oxide)

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

A glass apparatus for the preparation of diisoamyl ether

A glass apparatus for the preparation of diisoamyl ether

A small amount of water is placed in the Dean-Stark apparatus. A mixture of 62 ml (50 g) of iso-amyl alcohol and with 4 ml (7 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 iso-amyl 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 iso-amyl alcohol will pass back into the flask. The heating is continued for 90 minutes and the temperature inside the flask rises to 148-150° 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 steam distilled and the distillate is transferred in the separatory funnel, the upper layer containing the crude ether mixed with a little unreacted iso-amyl alcohol is separated, washed twice water, dried with anhydrous potassium carbonate, filtered into a 50 ml distilling flask, and purified by distillation. The fractions boiling at (I) 35-150° C (14 g), (II) 150-168° C (10 g) and (III) 168-174° C (10 g) are collected. The fractions (I) and (II) are combined, refluxed for 1 hour in a small flask with 3 g of sodium and distilled from the sodium isoamyloxide (sodium 3-methylbutan-1-olate) and excess of sodium yielding fairly pure diisoamyl ether. The total yield is therefore 24 g. A perfectly pure product, b.p. 170-171.5° C, is obtained by further distillation from a little sodium.

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

IUPAC Name

3-methyl-1-(3-methylbutoxy)butane

InChI

InChI=1S/C10H22O/c1-9(2)5-7-11-8-6-10(3)4/h9-10H,5-8H2,1-4H3

InChI Key

AQZGPSLYZOOYQP-UHFFFAOYSA-N

Canonical SMILES

CC(C)CCOCCC(C)C

Depositor-Supplied Synonyms

Isoamyl ether, Diisoamyl ether, Isopentyl ether, Diisopentyl ether, 544-01-4, Isoamyl oxide, Di-3-methylbutyl ether, DI-ISO-AMYL ETHER, Butane, 1,1′-oxybis[3-methyl-, 3-methyl-1-(3-methylbutoxy)butane, NSC 9281, 1,1′-Oxybis(3-methylbutane), 1,1′-Oxylbis(3-methylbutane), HSDB 2773, AQZGPSLYZOOYQP-UHFFFAOYSA-N, Butane, 1,1′-oxybis(3-methyl-, Butane, 1,1′-oxylbis(3-methyl-, EINECS 208-857-4, AI3-02268, i-pentylether, Diisopentylether, di-isoamyl ether, ACMC-209stu, di(3-methylbutyl) ether, AC1L1WDZ, DSSTox_CID_30769, DSSTox_GSID_52198, SCHEMBL42956, Butane,1′-oxybis[3-methyl-, 1-isopentyloxy-3-methyl-butane, UNII-5X9P91566R, CTK3J0478, NSC9281, MolPort-001-783-777, LTBB002271, NSC-9281, 1-(Isopentyloxy)-3-methylbutane #, Tox21_303780, 5776AF, ANW-41632, STL280333, ZINC01699894, AKOS009031402, 5X9P91566R, MCULE-3239546161, RTR-033489, TRA0081315, NCGC00357071-01, AN-45789, CAS-544-01-4, KB-49945, LS-45945, DB-052564, TR-033489, FT-0624975, I0086, I14-10603, InChI=1/C10H22O/c1-9(2)5-7-11-8-6-10(3)4/h9-10H,5-8H2,1-4H

Removed Synonyms

CID10989

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