Synthesis of hexyl methyl ether

Preparation of hexyl methyl ether (1-methoxyhexane; hexane, 1-methoxy-; methyl hexyl ether; ether, hexyl methyl)

Preparation of hexyl methyl ether (1-methoxyhexane; hexyl methyl ether; hexane, 1-methoxy-; methyl hexyl ether; ether, hexyl methyl)

Preparation of hexyl methyl ether (1-methoxyhexane; hexane, 1-methoxy-; methyl hexyl ether; ether, hexyl methyl)

A 500-ml two neck round bottom is fitted with a reflux condenser and a dropping funnel. 249.5 ml (204 g) of dry n-hexyl 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 125-126° 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 125-126° C. The two distillates are combined, the crude ether is removed from n-hexyl 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 hexyl methyl ether fraction boiling at 125-126° C is collected yielding 30 grams of final product. If the sodium is appreciably attacked, indicating that all the n-hexyl 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-methoxyhexane

InChI

InChI=1S/C7H16O/c1-3-4-5-6-7-8-2/h3-7H2,1-2H3

InChI Key

ICBJCVRQDSQPGI-UHFFFAOYSA-N

Canonical SMILES

CCCCCCOC

MeSH Synonyms

1-methoxyhexane, hexyl methyl ether, methyl hexyl ether

Depositor-Supplied Synonyms

1-Methoxyhexane, Hexyl methyl ether, Hexane, 1-methoxy-, 4747-07-3, Methyl hexyl ether, Ether, hexyl methyl, methoxyhexane, SBB061157, Methyl-n-Hexyl ether, n-Hexyl Methyl Ether, N-HEXYLMETHYLETHER, ACMC-2097gb, UNII-R99K6ANQ7T, AC1L2VC1, AC1Q58VB, R99K6ANQ7T, SCHEMBL57897, SCHEMBL6851067, CTK3J2189, ICBJCVRQDSQPGI-UHFFFAOYSA-, ICBJCVRQDSQPGI-UHFFFAOYSA-N, MolPort-000-557-716, EINECS 225-263-0, ANW-13929, AR-1C4275, ZINC02560611, AKOS002314381, AS00996, MCULE-7148964901, AN-19063, RT-000359, ST50758686, 3B3-052749, I14-112269, InChI=1/C7H16O/c1-3-4-5-6-7-8-2/h3-7H2,1-2H3

Removed Synonyms

CID78484, H0930, 5005-04-9

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