N-methyl-2-pyrrolidone → HCID 13548200, compound

Participants

Reaction Steps

16.0 g (0.07 mol) of the 3-bromo-4-n-butylphenol prepared in Step IV was dissolved in 70 ml of N-methyl-2-pyrrolidone. 6.5 g (0.073 mol) cuprous cyanide was added to the suspension which was refluxed for four hours. The reaction mixture was cooled to room temperature and poured into a solution of 26 g ferric chloride hexahydrate dissolved in a mixed solution of 10 ml of concentrated hydrochloric acid and 47 ml of water. The resultant solution was stirred with heating for 30 minutes at 65° C. in order to decompose nitrile complexes with cuprous bromide. Next, the suspension was poured into 300 ml of cold water, and an organic layer which separated out was extracted with ether. After the organic layer was clearned with acid, alkali and water and was dehydrated with anhydrous sodium sulfate, ether in the organic layer was distilled off. The residue was distilled under vacuum (115° C./1 mmHg) to yield 8.4 g of purified 3-cyano-4-n-butylphenol. The yield was calculated to be 68.2%.

Provenance & Evidence