Sulfuric Acid → HCID 56952340, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-chlorophenyacetonitrile (1 gr. 5.37 mmol), DBU (14 mg) and acetone (2 mL) was warmed to reflux for ˜6-7 minutes, cooled, and diluted with 3 mL of butyl chloride. The solution was treated with 3 drops of 3N HCl, washed with water and saturated NaCl solution and the organic layer was filtered through a small pad of anhydrous magnesium sulfate. The resulting solution was chilled to −50° C. and seeded with the starting nitrile. After crystallization was complete, the supernatant liquid was withdrawn. The resulting wet solid was allowed to partially melt, then re cooled and again the supernatant liquid was withdrawn The solid was allowed to melt and stripped of solvent to return 0.75 g starting nitrile which was retreated with acetone and DBU, reacted and worked up as above. The combined supernatant was stripped to an oil. This was dissolved in one mL of acetonitrile, treated with 0.3 mL of acetic anhydride, then stirred with a m.p. tube with tip wetted with conc. H2SO4 to give a slow exotherm to ˜35° C. This was heated briefly to ˜80° C., cooled, and 0.5 mL of ethanol added to remove excess acetic anhydride. The mixture was diluted with 3 mL of ethyl acetate, washed with water, dried (MgSO4) and stripped to an oil. The oil was purified by radial chromatography using butyl chloride followed by a hexane-ethyl acetate gradient. Stripping pure fractions returned 110 mg. Rf 0.4 (silica gel, EtOAc/hexane=¼) of the desired ester.

Provenance & Evidence