Synthesis of isobutyl chloride

Preparation of isobutyl chloride (1-chloro-2-methylpropane;  propane, 1-chloro-2-methyl-)

Preparation of isobutyl chloride (1-chloro-2-methylpropane;  propane, 1-chloro-2-methyl-)

Preparation of isobutyl chloride (1-chloro-2-methylpropane; propane, 1-chloro-2-methyl-)

500 ml round-bottomed flask is fitted with a dropping funnel and a double surface condenser. 46 ml (or 37 grams) of isobutyl alcohol (2-methyl-1-propanol) (b.p. 106-108° C) and 41 ml (or 40 grams) of pure pyridine are placed in the reaction flask. 73 ml (or 119 grams) of freshly distilled thionyl chloride are added to the dropping funnel, which is protected with calcium chloride tube into the mouth of the funnel. The thionyl chloride is dropwise added during 3-4 hours and a white solid separates, which partially dissolves as the reaction proceeds. Then the reaction mixture is refluxed for 45 minutes and the solid dissolves completely. The flask is cooled and the upper layer of alkyl chloride is separated, washed cautiously with water, 5% sodium hydroxide solution, then twice with water and dried with anhydrous calcium chloride. The crude isobutyl chloride is purified by distillation through an efficient fractionating column. The fraction boiling at 68-69° C is collected yielding 26 grams of pure isobutyl chloride. The lower pyridine layer contains most of the excess of thionyl chloride; it may be recovered by distillation through an efficient fractionating column.

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

IUPAC Name

1-chloro-2-methylpropane

InChI

InChI=1S/C4H9Cl/c1-4(2)3-5/h4H,3H2,1-2H3

InChI Key

QTBFPMKWQKYFLR-UHFFFAOYSA-N

Canonical SMILES

CC(C)CCl

Depositor-Supplied Synonyms

1-Chloro-2-methylpropane, ISOBUTYL CHLORIDE, 513-36-0, Propane, 1-chloro-2-methyl-, QTBFPMKWQKYFLR-UHFFFAOYSA-N, iso-C4H9Cl, sJPHADIKUP@, ACMC-1AKDY, AC1Q1PDE, 1-chloro-2-methyl-propane, AC1L1VG4, Propane,1-chloro-2-methyl-, KSC491K9J, 178004_ALDRICH, CHEMBL160966, UNII-95E08D17M7, CTK3J1594, MolPort-001-783-741, LTBB002440, EINECS 208-157-9, ANW-31239, STL264208, AKOS000119822, 95E08D17M7, MCULE-6524976746, RP18561, RTC-030983, TRA0068665, AN-23497, CJ-32017, KB-11909, SC-25552, DB-050395, TC-030983, FT-0607604, 3B4-0469, I14-4999, InChI=1/C4H9Cl/c1-4(2)3-5/h4H,3H2,1-2H

Removed Synonyms

2-Chloro-2-methylpropane, CID10554, c0207

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