Synthesis of amyl ether

Preparation of amyl ether

Alternative Names: pentyl ether; dipentyl ether; diamyl ether; n-pentyl ether; pentyloxypentane

Preparation of amyl ether (pentyl ether; dipentyl ether; diamyl ether; n-pentyl ether; pentyloxypentane;)

Preparation of amyl ether (pentyl ether; dipentyl ether; diamyl ether; n-pentyl ether; pentyloxypentane;)

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

A glass apparatus for the preparation of n-amyl ether

A glass apparatus for the preparation of n-amyl ether

A small amount of water is placed in the Dean-Stark apparatus. A mixture of 61.5 ml (50 g) of n-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 n-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 n-amyl alcohol will pass back into the flask. The heating is continued for 90 minutes and the temperature inside the flask rises to 157° 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 n-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) 145-175° C (13 g), (II) 175-185° C (8 g) and (III) 185-190° C (largely 185-185· 5° C) (13 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 amyloxide and excess of sodium yielding 9.5 g of fairly pure n-amyl ether. The total yield is therefore 22.5 g. A perfectly pure product, b.p. 184-185° 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

1-pentoxypentane

InChI

InChI=1S/C10H22O/c1-3-5-7-9-11-10-8-6-4-2/h3-10H2,1-2H3

InChI Key

AOPDRZXCEAKHHW-UHFFFAOYSA-N

Canonical SMILES

CCCCCOCCCCC

MeSH Synonyms

pentyl ether

Depositor-Supplied Synonyms

Pentyl ether, Amyl ether, Dipentyl ether, Diamyl ether, n-Pentyl ether, Pentyloxypentane, Pentane, 1,1′-oxybis-, 693-65-2, n-Amyl ether, Di-n-amyl ether, Di-n-pentyl ether, Ether, di-n-pentyl-, 1,1′-oxydipentane, NSC 6571, 1,1′-OXYBISPENTANE, AOPDRZXCEAKHHW-UHFFFAOYSA-N, EINECS 211-756-8, BRN 1698030, AI3-02267, pentylether, Dipentylether, 1-pentoxypentane, Pentane,1′-oxybis-, 1-(Pentyloxy)pentane #, ACMC-1BE2J, SCHEMBL8773, UNII-4G19C1NH3E, 4G19C1NH3E, AC1L209G, 42570_FLUKA, CTK2F3105, NSC6571, (n-C5H11)2O, MolPort-001-783-776, 42570_SIAL, NSC-6571, 5775AF, ANW-35649, ZINC01693640, AKOS015902356, TRA0009631, CJ-28362, LS-102291, TL8004855, TR-023084, A0451, ST50824706, I14-19521

Removed Synonyms

CID12743, 4-01-00-01643 (Beilstein Handbook Reference)

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