Methyl iodide → HCID 21533737, compound

Participants

Reaction Steps

Methyl 5-p-chlorophenylthien-2-ylacetate (1 g.) was dissolved in dry dioxan (10 ml.). Sodium hydride (0.1 g.) was added, the mixture was stirred for 30 minutes, and methyl iodide (0.6 g.) was then added. The mixture was refluxed for 30 minutes, cooled, and further sodium hydride (0.1 g.) and methyl iodide (1.1 ml.) were added. The mixture was refluxed for 2 hours, cooled and evaporated in vacuo to give an oil which was chromatographed on a column of Florisil (column: 9 inches long × 1 inch diameter) which was eluted with a mixture of equal volumes of benzene and petroleum ether (b.p. 60°-80°C.). The first 350 ml. of eluate was evaporated in vacuo to give an oil. This oil, which was mainly methyl α,α-dimethyl-α-(5-p-chlorophenylthien-2-yl)acetate, was hydrolysed by conventional means and gave α,α -dimethyl-α-(5-p-chlorophenylthien-2yl)-acetic acid, m.p. 146°-148°C.

Provenance & Evidence