3,4-Dihydroxy-1,6-bis(4-methoxyphenyl)hexa-2,4-diene-1,6-dione, its 4-methylphenyl analogue, and a potassium salt of 2-hydroxy-4-(4-methoxyphenyl)-4-oxobut-2-enoic acid

Abstract

Reaction of 4-methoxyacetophenone with diethyl oxalate under basic conditions produced 3,4-dihydroxy-1,6-bis(4-methoxyphenyl)hexa-2,4-diene-1,6-dione, C20H18O6, (1). The molecules lie across a crystallographic inversion centre and intramolecular hydrogen bonding, similar to acetylacetone, is observed, confirming that the molecule is in the di-enol-dione tautomeric form. Additional O-H...O hydrogen bonds link the molecules into chains parallel to the b axis. The structure is compared with that of redetermined 4-methylphenyl compound 3,4-dihydroxy-1,6-bis(4-methylphenyl)hexa-2,4-diene-1,6-dione, C20H18O4, (2), which crystallizes in a similar fashion. The salt, catena-poly[[μ2-2-hydroxy-4-(4-methoxyphenyl)-4-oxobut-2-enoato-κ(3)O(1),O(2):O(4)][μ2-2-hydroxy-4-(4-methoxyphenyl)-4-oxobut-2-enoic acid-κ(2)O(1):O(4)]potassium], [K(C11H9O5)(C11H10O5)]n, (3), was isolated as a by-product of the synthesis of (1). The two organic species are linked by a strong hydrogen bond between the carboxylic acid and carboxylate groups. They are further stabilized and linked into a double-chain structure via the seven-coordinate potassium ion.