Synthesis of n-butyl ethyl ether

Preparation of n-butyl ethyl ether

Preparation of n-butyl ethyl ether

Preparation of n-butyl ethyl ether

To prepare n-butyl ethyl 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 ethyl iodide (or ethyl bromide), and the mixture is heated under reflux with stirring and exclusion of moisture for 5 hours. 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. The yield of n-butyl ethyl ether 80%; n20/D 1.382; b.p. 91-92 °C; m.p. −124 °C; d=0.75 g/mL at 25 °C.

Organicum. Practical Handbook of Organic Chemistry, by Heinz Becker, Werner Berger and Günter Domschke, Addison-Wesley Pub. Co, 208-210, (1973)

IUPAC Name

1-ethoxybutane

InChI

InChI=1S/C6H14O/c1-3-5-6-7-4-2/h3-6H2,1-2H3

InChI Key

PZHIWRCQKBBTOW-UHFFFAOYSA-N

Canonical SMILES

CCCCOCC

Depositor-Supplied Synonyms

BUTYL ETHYL ETHER, 628-81-9, 1-Ethoxybutane, Butane, 1-ethoxy-, Ethyl butyl ether, Ether, butyl ethyl, n-Butyl ethyl ether, 1-Butyl ethyl ether, Ether ethylbutylique, Ether ethylbutylique [French], EINECS 211-055-7, UN1179, Butylethylether, 1-ethoxy-butane, Ethyl n-butyl ether, Ethyl-n-butyl Ether, PubChem12525, ACMC-1AWLV, AC1L1ZEX, DSSTox_CID_30883, n-C4H9OC2H5, UNII-NO396R19PJ, DSSTox_GSID_52311, SCHEMBL43234, 268925_ALDRICH, NO396R19PJ, SCHEMBL4637696, CTK2F5305, MolPort-000-152-573, PZHIWRCQKBBTOW-UHFFFAOYSA-N, ZINC2031618, Tox21_303804, ANW-34429, ZINC02031618, UN 1179, VZ21322, NCGC00357088-01, CAS-628-81-9, CJ-31762, LP100320, LS-67778, OR000277, TC-123174, TL8004302, B0776, FT-0626211, Ethyl butyl ether [UN1179] [Flammable liquid], A834065, Ethyl butyl ether [UN1179] [Flammable liquid], 3B3-009597

Removed Synonyms

CID12355, THIOCYANIC ACID, BUTYL ESTER

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