Potassium Cyanide → 3-Butyl-6-cyano-phthalide

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Reaction Steps

A suspension of 7.2 g (32.12 mmol) of the compound obtained in Example 4 in 100 ml of 18% hydrochloric acid is diazotized by a solution of 6 g of sodium nitrite in 30 ml of water at 3-5° C. To this solution there is added, with vigorous stirring, a solution of cuprous cyanide, prepared from 21.0 g of CuSO4.5H2O in 87 ml of H2O and 24.7 g of potassium cyanide in 133 ml of H2O at 50-60° C. The mixture is stirred at the same temperature for 2 hours. The separated solid is extracted with methylene chloride, the organic phase is washed with sodium carbonate solution and water. After removing the solvent, the residue is crystallised from ethanol to give the title compound.

Provenance & Evidence