Sodium hydride → HCID 22168537, compound

Participants

Reaction Steps

A 4.50 g portion of p-hydroxyphenylacetone, prepared above, was dissolved in 80 mL of anhydrous dimethylformamide under a dry nitrogen atmosphere. With stirring 1.26 g of sodium hydride (as a 60% dispersion in oil) was added to the solution. After 3 minutes, 9.40 g of 1-chloro-3-iodopropane was quickly added. After stirring for approximately 18 hours, the reaction was diluted with 300 mL hexane and 100 mL diethyl ether. The resulting mixture was washed with distilled water, 5% sodium hydroxide solution, and brine. The remaining organic phase was dried and evaporated to dryness in vacuo. The yellow oil was purified by column chromatography over silica gel, using 22% ethyl acetate and 78% hexane. Appropriate fractions were pooled and solvents removed in vacuo to yield 3.06 g of a yellow oil.

Provenance & Evidence