Methyl 3-mercaptopropionate → 3-(4,5-Dihydroxy-10-oxo-9,10-dihydro-anthracen-9-ylsulfanyl)-propionic acid methyl ester

Participants

Reaction Steps

10-Bromo-1,8-dihydroxy-9-anthrone (122 mg) was dissolved in dichloromethane (8 ml) and then methyl 3-mercaptopropionate (0.05 ml) was added. The red-brown solution became yellow-green immediately after addition of the thiol. The solution was stirred at room temperature for 5 hours. Removal of the solvent and recrystallisation of the residue from hexane gave the product (107.5 mg, 78%) as yellow needles, melting point 92°-94° C. (with decomposition). (Found: C 62.9, H 4.7, S 9.4%. C18H16O5S requires C 62.8, H 4.7, S 9.3%).

Provenance & Evidence