3-(4-Ethoxy­benzo­yl)propionic acid

Sajid Ali; Aurangzeb Hasan; Nasim Hasan Rama; Amir Badshah; Ales Ruczika

doi:10.1107/S1600536808034429

. 2008 Oct 25;64(Pt 11):o2206. doi: 10.1107/S1600536808034429

3-(4-Ethoxybenzoyl)propionic acid

Sajid Ali ^a, Aurangzeb Hasan ^a,^*, Nasim Hasan Rama ^a, Amir Badshah ^a, Ales Ruczika ^b

PMCID: PMC2959554 PMID: 21581064

Abstract

The title compound, C₁₂H₁₄O₄, is an important intermediate in the synthesis of biologically active heterocyclic compounds. In the crystal structure, intermolecular O—H⋯O and C—H⋯O hydrogen bonds link the molecules. There are also C—H⋯π contacts between the benzene ring and the methylene groups.

Related literature

For general background, see: Hashem et al. (2007 ▶); Husain et al. (2005 ▶). For bond-length data, see: Allen et al. (1987 ▶). graphic file with name e-64-o2206-scheme1.jpg

Experimental

Crystal data

C₁₂H₁₄O₄
M _r = 222.23
Triclinic,
a = 7.8371 (3) Å
b = 8.7399 (5) Å
c = 9.8140 (5) Å
α = 106.993 (4)°
β = 107.541 (4)°
γ = 107.142 (4)°
V = 556.34 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 150 (1) K
0.34 × 0.32 × 0.31 mm

Data collection

Bruker–Nonius KappaCCD area-detector diffractometer
Absorption correction: Gaussian (Coppens, 1970 ▶) T _min = 0.964, T _max = 0.987
8993 measured reflections
2508 independent reflections
2089 reflections with I > 2σ(I)
R _int = 0.059

Refinement

R[F ² > 2σ(F ²)] = 0.047
wR(F ²) = 0.123
S = 1.11
2508 reflections
145 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: COLLECT and DENZO (Otwinowski & Minor, 1997 ▶); data reduction: COLLECT and DENZO; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808034429/hk2555sup1.cif

e-64-o2206-sup1.cif^{(15.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808034429/hk2555Isup2.hkl

e-64-o2206-Isup2.hkl^{(123.2KB, hkl)}

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
O2—H2⋯O1ⁱ	0.82	1.85	2.664 (3)	172
C2—H2B⋯O3ⁱⁱ	0.97	2.44	3.386 (3)	165
C11—H11B⋯O3ⁱⁱⁱ	0.97	2.50	3.445 (3)	166
C3—H3B⋯Cg1^iv	0.97	2.66	3.528 (3)	150
C11—H11A⋯Cg1^v	0.97	2.84	3.679 (3)	145

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) ; (v) . Cg1 is the centroid of the phenyl ring.

Acknowledgments

The authors gratefully acknowledge funds from the Higher Education Commission, Islamabad, Pakistan.

supplementary crystallographic information

Comment

Benzoyl propionic acids are important intermediates in heterocyclic chemistry and have been used for the synthesis of various biologically active five -membered heterocyles such as butenolides, pyrrolones (Husain et al., 2005), oxadiazoles and triazoles (Hashem et al., 2007). In view of the versatility of these compounds, we synthesized the title compound and reported herein its crystal structure.

In the title compound (Fig. 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges . O4, C2, C3, C4, C11 and C12 atoms are -0.011 (3), 0.162 (4), 0.189 (4), -0.09 (3), -0.143 (3) and -0.151 (3) Å away from the phenyl plane, respectively.

In the crystal structure, intermolecular O-H···O and C-H···O hydrogen bonds (Table 1) link the molecules (Fig. 2), in which they may be effective in the stabilization of the structure. There also exist C—H···π contacts (Table 1) between the phenyl ring and the methylene groups.

Experimental

The title compound was synthesized by the condensation of succinic anhydride (2 g, 20 mmol) with 1-ethoxybenzene (10 ml) in the presence of alumium chloride (6 g, 42 mmol). The reaction mixture was refluxed for 4 h. After completion of the reaction, excess solvent (Anisol) was removed by steam distillation. The resultant solid product was purified by dissolving it in sodium hydroxide solution (5%, w/v), filtering followed by addition of hydrochloric acid. The obtained solid mass was filtered, washed with cold water, dried and crystallized from methanol (yield; 67%, m.p. 404-405 K).