Synthesis of n-hexyl chloride

Preparation of n-hexyl chloride

Alternative Names: 1-chlorohexane; chlorohexane; hexyl chloride

Preparation of n-hexyl chloride (1-chlorohexane; chlorohexane; hexyl chloride)

Preparation of n-hexyl chloride (1-chlorohexane; chlorohexane; hexyl chloride)

500 ml round-bottomed flask fitted with a dropping funnel and a double surface condenser is charged with 109.5 ml (or 179 grams) of freshly distilled thionyl chloride. 62 ml (or 52 grams) of n-hexyl alcohol (b.p. 156-158° C) are placed in the dropping funnel. The n-hexyl alcohol is dropwise added during 2 hours. During the addition there is a slight evolution of heat, sulfur dioxide evolves and the liquid darkens considerably. When all the hexyl alcohol has been added, the reaction mixture is refluxed for 2 hours. The obtained reaction mixture is distilled and the excess of thionyl chloride passes over below 80° C, followed by a small fraction up to 120° C. Finally, the crude n-hexyl chloride distils at 132-134° C. The purified n-hexyl chloride is washed with water, 10% sodium carbonate solution, twice with water and dried with anhydrous calcium chloride. n-Hexyl chloride is additionally purified by distillation through an efficient fractionating column. Pure n-hexyl chloride passes over at 133-134° C. The yield is 36 grams.

A text book of practical organic chemistry, by A. I. Vogel, 274, 1974

IUPAC Name

1-chlorohexane

InChI

InChI=1S/C6H13Cl/c1-2-3-4-5-6-7/h2-6H2,1H3

InChI Key

MLRVZFYXUZQSRU-UHFFFAOYSA-N

Canonical SMILES

CCCCCCCl

MeSH Synonyms

1-chlorohexane

Depositor-Supplied Synonyms

1-CHLOROHEXANE, Chlorohexane, Hexyl chloride, 544-10-5, Hexane, 1-chloro-, n-Hexyl chloride, 1-Chloro-hexane, Hexane, chloro-, MLRVZFYXUZQSRU-UHFFFAOYSA-N, SBB059952, 25495-90-3, hexylchloride, 1-chloranylhexane, 1-Hexyl chloride, normal-Hexyl chloride, Triisobutenyl chloride, ACMC-1BMPH, UNII-R5L7I6O9NW, AC1L1WE5, R5L7I6O9NW, SCHEMBL51706, KSC202S5T, 238465_ALDRICH, CHEMBL156095, QSPL 014, 24770_FLUKA, 24771_FLUKA, CTK1A2959, MLRVZFYXUZQSRU-UHFFFAOYSA-, MolPort-001-783-742, EINECS 208-859-5, ANW-32067, ZINC02013436, AKOS009156950, RTR-019239, TRA0079084, AN-21356, CJ-07367, CJ-31202, KB-11965, 1-Propene, 2-methyl-, trimer, chlorinated, AI3-28589, DB-052566, TR-019239, FT-0602988, FT-0632356, ST51046217, 119347-EP2289965A1, 119347-EP2298828A1, A830166, I09-1084, I14-92499, 3B3-020142, InChI=1/C6H13Cl/c1-2-3-4-5-6-7/h2-6H2,1H3, 61383-30-0, 70776-07-7

Removed Synonyms

CID10992, c0184

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