Dimethyl Sulfate → HCID 54443769, compound

Participants

Reaction Steps

4 g of bis(3-hydroxy-5,5-dimethyl-4,6-dioxocyclohex-2-enylidene)ethane (from Example 3) were dissolved in a mixture of 240 ml of dioxane and 240 ml of acetonitrile by refluxing under nitrogen. 16 g of dimethyl sulfate were then added, followed by 12 g of finely crushed anhydrous potassium carbonate. The batch turned greenish blue at once, but became yellow in the course of an hour of heating under reflux. The reaction mixture was filtered while still hot, the filter cake was washed with acetonitrile, and the combined organic phases were concentrated in a rotary evaporator. The residues of alkylating agent were removed by digestion with ether, and the insolubles were removed by heating in chloroform. The filtrate was concentrated and the residue was repeatedly recrystallized from acetone. This gave a solid in the form of reddish yellow prisms.

Provenance & Evidence