Sulfuric Acid → HCID 22664370, compound

Participants

Reaction Conditions

Reaction Steps

To a 2 L, five-necked flask equipped with a mechanical stirrer, 500 mL of 2-butanol and 8 g of sodium hydroxide pellets are charged and heated to 90° C. A solution of 50 g of the monoazo compound prepared in Example 12, 2.3 g of 2,3-dichloro-1,4-naphthoquinone and 300 mL of heptane is charged to the hot butanol solution over a three hour period. After the addition is complete, the reaction mass is stirred for an additional hour at reflux. To the reaction mass is then added, 100 mL of water and the pH is adjusted to 2 with 30% aqueous sulfuric acid. The aqueous layer is removed and the organic layer is washed once with 100 mL of saturated sodium chloride solution and twice with water. The desired product is crystallized from the solution yielding the title compound as a light yellow solid melting at 140° C. The structure is verified by 1Hnmr and mass spectroscopy analyses.

Provenance & Evidence