5-Meth­oxy-2-benzofuran-1(3H)-one

Drielly A Paixão; Silvana Guilardi; Jorge L Pereira; Róbson R Teixeira; Júnior F Arantes

doi:10.1107/S1600536812044789

. 2012 Nov 7;68(Pt 12):o3288. doi: 10.1107/S1600536812044789

5-Methoxy-2-benzofuran-1(3H)-one

Drielly A Paixão ^a, Silvana Guilardi ^a,^*, Jorge L Pereira ^b, Róbson R Teixeira ^b,^*, Júnior F Arantes ^b

PMCID: PMC3588834 PMID: 23468799

Abstract

In the title compound, C₉H₈O₃, the molecular skeleton is almost planar, with an r.m.s. deviation of 0.010 (2) Å. In the crystal, weak C—H⋯O hydrogen bonds connect the molecules into a two-dimensional network parallel to the ac plane.

Related literature

For the biological activity of isobenzofuran-1(3H)-one, see: Ma et al. (2012 ▶); Huang et al. (2012 ▶); Zhao et al. (2012 ▶); Arnone et al. (2002 ▶). For the synthesis, see: Zhang et al. (2009 ▶). For related structures, see: Sun et al. (2009 ▶); Mendenhall et al. (2003 ▶); Pereira et al. (2012 ▶). graphic file with name e-68-o3288-scheme1.jpg

Experimental

Crystal data

C₉H₈O₃
M _r = 164.15
Monoclinic,
a = 8.1819 (9) Å
b = 10.4285 (18) Å
c = 9.2965 (9) Å
β = 99.962 (8)°
V = 781.26 (18) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 293 K
0.30 × 0.18 × 0.16 mm

Data collection

Enraf–Nonius KappaCCD diffractometer
14100 measured reflections
1587 independent reflections
1101 reflections with I > 2σ(I)
R _int = 0.049

Refinement

R[F ² > 2σ(F ²)] = 0.049
wR(F ²) = 0.147
S = 1.06
1587 reflections
109 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.13 e Å⁻³

Data collection: COLLECT (Nonius, 2000 ▶); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 ▶); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Click here for additional data file.^{(18.1KB, cif)}

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812044789/zs2239sup1.cif

e-68-o3288-sup1.cif^{(18.1KB, cif)}

Click here for additional data file.^{(78.2KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812044789/zs2239Isup2.hkl

e-68-o3288-Isup2.hkl^{(78.2KB, hkl)}

Click here for additional data file.^{(3.3KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536812044789/zs2239Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O1ⁱ	0.93	2.54	3.419 (2)	157
C8—H8A⋯O2ⁱⁱ	0.97	2.52	3.372 (2)	146

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

The authors thank Professor Dr Javier Ellena of the IFSC, USP, Brazil, for the X-ray data collection. This work was supported financially by CAPES, CNPq, FUNARBE and FAPEMIG. This work is also a collaboration research project of members of the Rede Mineira de Química (RQ - MG) also supported by FAPEMIG.

supplementary crystallographic information

Comment

Isobenzofuran-1(3H)-ones (phthalides) are a class of heterocyclic compounds which occur in several natural products and have been investigated for several biological properties, such as antiplatelet (Ma et al., 2012) and antioxidant activities (Huang et al., 2012), inhibition of glutamate induced cytotoxicity in PC12 cells (Zhao et al., 2012) and phytotoxicity (Arnone et al., 2002). The title compound, C₉H₈O₃ was obtained as an intermediate in a synthetic route in the preparation of compounds endowed with phytotoxic activity and we report the crystal structure of it in a continuation of our work on the synthesis of phthalides (Pereira et al., 2012).

The title molecule (Fig. 1) is essentially planar with a mean deviation of 0.010 (2) Å from the least squares plane traced by 12 non-H atoms. All bond distances and angles agree well with those reported in the related compounds (Sun et al., 2009; Mendenhall et al., 2003; Pereira et al., 2012). In the crystal, molecules are linked via weak C6—H6···O1 hydrogen bonds (Table 1) forming chains along the ac plane. These layers are extended by C8—H8A···O2 hydrogen bonds into a two-dimensional network structure (Fig. 2).

Experimental

Starting materials were commercially available from Sigma Aldrich (USA) and were used without further purification. 5-Methoxyisobenzofuran-1(3H)-one was prepared as follows (Zhang et al., 2009). A tube of 40 ml equipped with a magnetic stir bar was charged with palladium(II) acetate (67.3 mg, 0.30 mmol), potassium bicarbonate (750 mg, 7.50 mmol), 4-methoxybenzoic acid (456 mg, 3.00 mmol) and dibromomethane (12 ml). The tube was sealed with a teflon cap and the reaction mixture was stirred at 140 °C for 18 h. After this time, the mixture was filtered through a pad of celite. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography eluted with hexane: ethyl acetate (2:1 v/v) to afford 5-methoxyisobenzofuran-1(3H)-one in 33% yield (164 mg, 1.00 mmol). The crystals suitable for X-ray crystallographic analysis were obtained by slow evaporation from acetone solution at room temperature as a yellow solid; m.p. 113.4–114.7 °C. IR (selected bands, cm^-1): 3032, 2922, 2852, 1736, 1601, 1489, 1452, 1361, 1333, 1261, 1146, 1036, 986, 773. ¹H NMR (300 MHz, CDCl₃): δ 3.89 (s, 3H, H9), 5.25 (s, 2H, H8), 6.91 (d, 1H, J = 0.6 Hz, H6), 7.02 (dd, 1H, J = 8.4, 0.6 Hz, H4), 7.80 (d, 1H, J = 8.4 Hz, H3). ¹³C NMR (75 MHz, CDCl₃): δ 56.1 (C9), 69.3 (C8), 106.2 (C6), 116.7 (C4), 118.2 (C2), 127.4 (C3), 149.6 (C7), 164.9 (C5), 171.1 (C1). HREIMS m/z (M+H⁺): Calcd for C₉H₈O₃, 165.0552; found: 165.0606.