Synthesis of n-heptyl chloride

Preparation of n-heptyl chloride

Alternative Names: 1-chloroheptane; heptane, 1-chloro-; chloroheptane

Preparation of n-heptyl chloride (1-chloroheptane; heptane, 1-chloro-; chloroheptane)

Preparation of n-heptyl chloride (1-chloroheptane; heptane, 1-chloro-; chloroheptane)

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.  70.5 ml (or 58 grams) of n-heptyl alcohol (b.p. 175-177° C) are placed in the dropping funnel. The n-heptyl 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 heptyl alcohol has been added, the reaction mixture is refluxed for 4 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-heptyl chloride distils at 159-160° C. The purified n-heptyl chloride is washed with water, 10% sodium carbonate solution, twice with water and dried with anhydrous calcium chloride. n-Heptyl chloride is additionally purified by distillation through an efficient fractionating column. Pure n-heptyl chloride passes over at 159-160° C. The yield is 52 grams.

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

IUPAC Name

1-chloroheptane

InChI

InChI=1S/C7H15Cl/c1-2-3-4-5-6-7-8/h2-7H2,1H3

InChI Key

DZMDPHNGKBEVRE-UHFFFAOYSA-N

Canonical SMILES

CCCCCCCCl

Depositor-Supplied Synonyms

1-CHLOROHEPTANE, Heptyl chloride, 629-06-1, n-Heptyl chloride, Heptane, 1-chloro-, chloroheptane, DZMDPHNGKBEVRE-UHFFFAOYSA-N, SBB059954, 1-chloro-heptane, 1-chloranylheptane, Heptane, chloro-, normal-Heptyl chloride, ACMC-1B1XE, AC1L1ZG9, SCHEMBL44335, KSC203O4J, UNII-2F3Z1E37X5, 109746_ALDRICH, CHEMBL1797136, 24740_FLUKA, CTK1A3744, MolPort-001-783-743, 2F3Z1E37X5, EINECS 211-070-9, ANW-34443, STL280514, AKOS000118768, MCULE-6286146566, AN-46923, KB-65033, DB-021161, RT-000644, TL8004313, FT-0607647, ST51046218, A834082, I14-6081, InChI=1/C7H15Cl/c1-2-3-4-5-6-7-8/h2-7H2,1H

Removed Synonyms

2-Chloroheptane, CID12371, c0182, 29756-37-4, 4398-65-6

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