(E)-4-(4-Meth­oxy­phen­yl)but-3-en-2-one

Ambika Sambyal; Manpreet Kour; Sumati Anthal; R K Bamzai; Rajni Kant; Vivek K Gupta

doi:10.1107/S1600536812012214

. 2012 Mar 24;68(Pt 4):o1183. doi: 10.1107/S1600536812012214

(E)-4-(4-Methoxyphenyl)but-3-en-2-one

Ambika Sambyal ^a, Manpreet Kour ^b, Sumati Anthal ^b, R K Bamzai ^a, Rajni Kant ^b, Vivek K Gupta ^b,^*

PMCID: PMC3344121 PMID: 22606124

Abstract

In the title compound, C₁₁H₁₂O₂, the dihedral angle between the benzene ring and the but-3-en-2-one group is 4.04 (5)°. The crystal packing features chains, parallel to [-101], composed of dimers connected by weak C—H⋯O interactions..

Related literature

For related structures, see: Jasinski et al. (2010 ▶); Fun et al. (2011 ▶); Dutkiewicz et al. (2011 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₁H₁₂O₂
M _r = 176.21
Monoclinic,
a = 10.1623 (19) Å
b = 13.292 (3) Å
c = 6.6488 (13) Å
β = 98.486 (3)°
V = 888.3 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 K
0.30 × 0.30 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.920, T _max = 0.980
4492 measured reflections
1556 independent reflections
1332 reflections with I > 2σ(I)
R _int = 0.057

Refinement

R[F ² > 2σ(F ²)] = 0.063
wR(F ²) = 0.150
S = 1.10
1556 reflections
121 parameters
H-atom parameters constrained
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.60 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; 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: PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812012214/gk2469sup1.cif

e-68-o1183-sup1.cif^{(18.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812012214/gk2469Isup2.hkl

e-68-o1183-Isup2.hkl^{(75.1KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812012214/gk2469Isup3.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′⋯O2ⁱ	0.93	2.52	3.296 (2)	141
C6—H6B⋯O2ⁱⁱ	0.96	2.57	3.533 (2)	176

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

Acknowledgments

The authors are thankful to Professor P. K. Bharadwaj, Department of Chemistry, IIT, Kanpur, India, for the single-crystal X-ray diffraction data. VKG is thankful to the University of Jammu, Jammu, India, for financial support.

supplementary crystallographic information

Comment

The title compound belongs to the class of unsaturated α,β- acyclic ketones. α,β- unsaturated ketones have been found useful in the preparation of a wide variety of nitrogen heterocycles both in solution phase and solid state. Many of these synthesis have proceeded through interesting mechanisms. These compounds have been used as substrates for the preparation of anti-cancer, cell-specific triarylpyridines via immobilized bismuth nitrate catalyzed cascade reactions. These compounds have been extensively used in the preparation of cardiovascular Hantzsch products, many of which are prescribed drugs. α,β- unsaturated ketones are easily elaborated to anti-anxiety diazepines which also regulate our central nervous system. When treated with hydrazine, α,β- unsaturated compounds yield substituted pyrazoles which have a wide spectrum of bioactivity. The molecular structure of the title compound is shown in Fig.1. The bond distances are within normal ranges (Allen et al., 1987) and comparable to those in related structures (Jasinski et al., 2010; Fun et al., 2011; Dutkiewicz et al., 2011). The six bond lengths in the benzene ring lie in the range 1.355 (2)–1.391 (2) Å with an average value of 1.372 (2) Å. The average bond angle of the phenyl ring is 120.0 (1)°. In the title compound the benzene ring is perfectly planar with a maximum deviation of 0.006 (2) Å for C2'. The dihedral angle between the benzene ring and the acyclic chain is 4.04 (5)°. In the crystal structure, intermolecular C—H···O hydrogen bonds link the molecules into chains (Fig.2).

Experimental

Normally, α,β-unsaturated compounds are prepared by the reaction of an aldehyde and an active methylene compounds by Claisen-Schmidt reaction, using a strong base or an acid as catalyst. Under these reaction conditions, aromatic aldehydes and acetone react hard to form diarylidene ketone by double Claisen condensation. Monocondensation processes are known but yields are poor. To improve yield of monocondensation products, a search for catalyst was undertaken and sodium tungstate in ethanol was found as the catalyst of choice. The title compound was prepared in 96% yield by stirring the mixture of anisaldehyde (1 X 10-2 mol) and acetone (1 X 10-2 mol) in the presence of sodium tungstate (30 mol %) using ethanol as solvent at room temperature (25°C) for 24h. The reaction was monitored by thin layer chromatography. On completion of the reaction, the reaction mixture was diluted with water (25ml) and extracted with ethyl acetate (50 ml). The organic layer was washed with water, brine and water, dried over anhydrous sodium sulphate and concentrated. The title compound was purified by column chromatography on silica gel, using CH₂Cl₂-EtOAC (9:1v/v) as solvent. The compound was crystallized from chloroform-methanol, m.p. 445K. Single crystals for XRD study were obtained by slow evaporation of chloroform solution.