Synthesis of 1-iodo-2,2-dimethylpropane

Preparation of 1-iodo-2,2-dimethylpropane

Methyl iodide (1.4 moles), triphenyl phosphite (1 mole), and neopentyl alcohol (1 mole) are heated in a bath for 24 hours, whereby, owing to continuing consumption of methyl iodide, the internal temperature rises from 75° to 130°. The crude 1-iodo-2,2-dimethylpropane and the phenol are distilled off in a vacuum and the distillate is washed with ice-cold, dilute sodium hydroxide solution, and water until free from phenol. The product contains about 6% of terf-pentyl iodide, to remove which it is shaken for 5 hours with three times its volume of water which is then discarded. The organic layer is next shaken with its own volume of 0.1N-aqueous silver nitrate, washed with water, dried, and fractionated. This gives a 53-57 % yield of 1-iodo-2,2-dimethylpropane of b.p. 71°/100 mm.

J. Chem. Soc, 1953, 2224.

J. Amer. Chem. Soc, 54, 749 (1932).

IUPAC Name

1-iodo-2,2-dimethylpropane

InChI

InChI=1S/C5H11I/c1-5(2,3)4-6/h4H2,1-3H3

InChI Key

CJTZXIJETZZARD-UHFFFAOYSA-N

Canonical SMILES

CC(C)(C)CI

Depositor-Supplied Synonyms

Neopentyl iodide, 1-Iodo-2,2-dimethylpropane, 15501-33-4, 2,2-Dimethyl-1-iodopropane, Propane, 1-iodo-2,2-dimethyl-, CJTZXIJETZZARD-UHFFFAOYSA-N, Neopentyliodide, NSC617421, 2,2-Dimethylpropyl iodide, ACMC-20ak50, AC1L38IL, AC1Q4PQ9, SCHEMBL77943, 1-iodo-2,2-dimethyl-propane, 301086_ALDRICH, CHEMBL1993907, DTXSID3065904, Propane,1-iodo-2,2-dimethyl-, CTK4C8493, ZINC1613314, EINECS 239-533-0, AR-1C4083, NSC-617421, KB-12633, NCI60_005259, OR049320, OR225525, DB-064067, TC-165771, FT-0659435, Q-201459, S14-1405

Removed Synonyms

CID84953, 15758-24-4

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