Sulfuric Acid → HCID 20504286, compound

Participants

Reaction Conditions

Reaction Steps

To the sodium salt of 3-ethynylphenol, prepared from 4.3 g (0.037 mole) of sodium methoxide was added 50 ml of dry N,N-dimethylacetamide, under nitrogen. The mixture was heated to 70° C. and 12.0 g (0.041 mole) of 4-nitro-N-(3-ethynylphenyl)-phthalimide was added. The dark mixture was stirred at 70° C. for 3 hours, then poured into 1.5 liters of ice water. About 100 ml of 1 N sulfuric acid was added to the cold mixture to precipitate the product. The precipitate was collected by filtration, air dried, dissolved in 100 ml of methylene chloride, than again filtered. Chromotography of the filtrate on silica gel using 1:1 hexane:methylene chloride as the eluent gave 5.8 g (44% yield) of product, m.p. 150°-160° C.

Provenance & Evidence