Synthesis of butyl methyl ether

Preparation of butyl methyl ether (1-methoxybutane; butane, 1-methoxy-; ether, butyl methyl; methyl butyl ether; methyl n-butyl ether)

A 500-ml two neck round bottom is fitted with a reflux condenser and a dropping funnel. 183 ml (148 g) of dry n-butyl 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). 15.5 ml (35.5 g) of methyl 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 70-71° C. 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 15.5 ml (35.5 g) of methyl iodide are introduced and the mixture is reflux for 2 hours. The apparatus is rearranged for distillation and the crude ether is collected at 70-71° C. The two distillates are combined, the crude ether is removed from n-butyl 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-butyl ether fraction boiling at 70-71° C is collected yielding 31 grams of final product. If the sodium is appreciably attacked, indicating that all the n-butyl 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-methoxybutane

InChI

InChI=1S/C5H12O/c1-3-4-5-6-2/h3-5H2,1-2H3

InChI Key

CXBDYQVECUFKRK-UHFFFAOYSA-N

Canonical SMILES

CCCCOC

Depositor-Supplied Synonyms

1-Methoxybutane, BUTYL METHYL ETHER, Butane, 1-methoxy-, Ether, butyl methyl, Methyl butyl ether, Methyl n-butyl ether, n-Butyl methyl ether, 628-28-4, butylmethylether, alpha-Methoxybutane, methylbutyl ether, CXBDYQVECUFKRK-UHFFFAOYSA-N, EINECS 211-033-7, UN2350, butyl methylether, buthyl methly ester, .alpha.-Methoxybutane, N-BUTYLMETHYLETHER, AC1L1ZDL, n-C4H9OCH3, ACMC-1AV11, Butane, 1-methoxy- (9CI), 235377_ALDRICH, CTK3J2218, MolPort-001-783-780, LTBB003765, ANW-34396, ZINC02031625, RTR-021614, UN 2350, LS-67781, TL8004278, TR-021614, M0504, 31877-EP2281813A1, 31877-EP2298734A2, 31877-EP2311816A1, 37261-EP2311802A1, 37261-EP2311803A1, 107683-EP2289879A1, 107683-EP2298746A1, Butyl methyl ether [UN2350] [Flammable liquid], Butyl methyl ether [UN2350] [Flammable liquid], InChI=1/C5H12O/c1-3-4-5-6-2/h3-5H2,1-2H

Removed Synonyms

CID12338

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