Synthesis of 1-methoxypentane

Preparation of 1-methoxypentane

Preparation of 1-methoxypentane

Preparation of 1-methoxypentane

To prepare 1-methoxypentane (n-pentyl methyl ether), an alkoxide solution is first prepared from 0.25 gramequivalent of metallic sodium and 1.2 mole of the absolute n-pentyl 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 1-methoxypentane is 80%, n20/D 1.3873; b.p. 99°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 a 30-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-methoxypentane

InChI

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

InChI Key

DBUJFULDVAZULB-UHFFFAOYSA-N

Canonical SMILES

CCCCCOC

Depositor-Supplied Synonyms

1-Methoxypentane, Methyl pentyl ether, Ether, methyl pentyl, Pentane, 1-methoxy-, Amyl methyl ether, Methyl amyl ether, Pentyl methyl ether, n-Amyl methyl ether, Butane, methoxymethyl-, 628-80-8, methoxypentane, SBB061300, BRN 1731334, AC1L2BT8, AC1Q58UY, n-C5H11OCH3, SCHEMBL57335, Pentane, 1-methoxy- (9CI), CTK1J3517, DBUJFULDVAZULB-UHFFFAOYSA-N, MolPort-035-880-627, LABOTEST-BB LTBB003767, ZINC1845902, AR-1C4281, ZINC01845902, AKOS006230257, AS01005, MCULE-3370181741, LP044773, LS-67867, OR309887, ST51047328, 67412-13-9

Removed Synonyms

CID69412, (Hydroxyethyloxy)tri(Ethyloxy)octane, 4-01-00-01643 (Beilstein Handbook Reference), 63896-87-7, C8E

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