3-Hydroxy-4-nitrophenyl acetate

In the molecule of the title compound, C8H7NO5, the acetate group is oriented with respect to the aromatic ring at a dihedral angle of 85.30 (3)°. An intramolecular O—H⋯O hydrogen bond results in the formation of a non-planar six-membered ring, adopting an envelope conformation. In the crystal structure, intermolecular C—H⋯O hydrogen bonds link the molecules.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HK2582).

Comment
Phenolic esters are useful intermediates in organic synthesis (Trollsås et al., 1996;Svensson et al., 1998;Atkinson et al., 2005;Hu et al., 2001). We have developed a new method for the syntheses of some phenolic esters (Ji et al., 2006). The title compound is one of the products, and we report herein its crystal structure.
In the molecule of the title compound ( Fig. 1) the bond lengths (Allen et al., 1987) and angles are within normal ranges. The acetate group is oriented with respect to the aromatic ring at a dihedral angle of 85.30 (3)°. The intramolecular O-H···O hydrogen bond (Table 1) results in the formation of a nonplanar six-membered ring (N1/O3/O4/C6/C7/H3), adopting envelope conformation.
In the crystal structure, intermolecular C-H···O hydrogen bonds (Table 1) link the molecules (Fig. 2), in which they may be effective in the stabilization of the structure.
At 273-278 K, anhydrous AlCl 3 (133.5 mg, 1 mmol) was added to this solution, the reaction was stirred at room temperature for 1 h, and then hydrochloric acid (5 ml, 10%) was added. The reaction mixture was extracted with chloroform and dried with anhydrous sodium sulfate. After concentration, the residue was separated by flash column chromatography and purified by recrystallization from chloroform (yield; 144 mg, 73%, m.p. 360 K). Spectroscopic analysis: IR (KBr, ν, cm -1 ): 3253,3083,2946,1758,1530,1204,1138,978,847 Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. Hydrogen bond is shown as ashed line. Fig. 2 Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > σ(F 2 ) is used only for calculating Rfactors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.