Synthesis of n-butyl methyl ether

Preparation of n-butyl methyl ether

Preparation of n-butyl methyl ether

Preparation of n-butyl methyl ether

To prepare n-butyl methyl ether, an alkoxide solution is first prepared from 0.25 gramequivalent of metallic sodium and 1.2 mole of the absolute n-butyl alcohol in a three-necked flask provided with a stirrer and reflux condenser. To the obtained alkoxide is added 0.2 mole of methyl iodide (alternatively methyl bromide or 0.14 mole of dimethyl sulfate), and the mixture is heated under reflux with stirring and exclusion of moisture for 5 hours. The yield of n-butyl methyl ether 80%, n20/D 1.374; b.p. 70-71 °C; m.p. −115 °C; d=0.744 g/mL at 25 °C. The reaction product is distilled off directly with stirring until the boiling point of the alcohol used is reached. The distillate, which consists of ether and the alcohol used, is fractionated into narrower fractions through a30-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-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-, Methyl butyl ether, Ether, butyl methyl, n-Butyl methyl ether, 628-28-4, Methyl n-butyl ether, butylmethylether, alpha-Methoxybutane, methylbutyl ether, CXBDYQVECUFKRK-UHFFFAOYSA-N, EINECS 211-033-7, UN2350, butoxymethyl, butyl methylether, buthyl methly ester, .alpha.-Methoxybutane, N-BUTYLMETHYLETHER, AC1L1ZDL, n-C4H9OCH3, ACMC-1AV11, Butane, 1-methoxy- (9CI), 235377_ALDRICH, CTK3J2218, LTBB003765, ZINC2031625, ANW-34396, ZINC02031625, MCULE-9814272675, RTR-021614, UN 2350, LP065807, LS-67781, OR035253, 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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