Cloricromen is a platelet aggregation inhibitor. Coronary vasodilator.
Synthesis
Base catalyzed alkylation of ethyl acetoacetate (1) with 2-chlorotriethylamine (2) gives compound (3). Separately, disulfonation of resorcinol (4) with 96% sulfuric acid gives the disulfonic acid (5). This is chlorinated with potassium chlorate to give 5-chloro-4,6-dihydroxybenzene-1,3-disulfonic acid (6). Removal of the sulfonate groups in dilute acid then gives 2-chlororesorcinol (7). An acid-catalyzed condensation reaction between (3) and (7) produces the intermediate (8). Ether formation at its phenolic hydroxyl group with ethyl bromoacetate (9) completes the synthesis of cloricromen.Francesco Della Valle, (1984 to Fidia S.P.A.).
See also Carbocromen is the analogue without the chlorine substituent References