Benzyl 2,6-dihydroxy-3-nitrobenzoate

Abstract

Crystals of the title compound, C14H11NO6, were obtained by the reaction of benzyl 2,6-dihydroxy­benzoate with nitric acid and crystallization of the product from ethyl acetate. In the mol­ecule, the nitro group is essentially coplanar with the attached benzene ring [O—N—C—C = 176.75 (11)°], indicating conjugation with the π-electron system. The benzyloxy group of the ester group is cis with respect to the 2-hydroxy group. The crystal structure is stabilized by intra- and inter­molecular hydrogen bonds. The 2-hydroxy group forms an intra­molecular hydrogen bond with the nitro group, and the 6-hydroxy group forms an intra­molecular hydrogen bond with the ester carbonyl function. In addition, there is inter­molecular hydrogen bonding between the 2-hydroxy group of one mol­ecule and the O atom of the 6-hydroxy group of another mol­ecule.