(E)-Methyl 2-benzyl-3-o-tolylacrylate

In the title compound, C18H18O2, the methyl acrylate substituent adopts an extended E conformation with all torsion angles close to 180°. The mean plane of the acrylate unit and the phenyl ring are approximately orthogonal to each other, making a dihedral angle of 81.40 (6)°. The position of the carbonyl group with respect to the olefinic double bond is typically S-trans. The crystal packing is stabilized by intermolecular C—H⋯π interactions.

In the title compound, C 18 H 18 O 2 , the methyl acrylate substituent adopts an extended E conformation with all torsion angles close to 180 . The mean plane of the acrylate unit and the phenyl ring are approximately orthogonal to each other, making a dihedral angle of 81.40 (6) . The position of the carbonyl group with respect to the olefinic double bond is typically S-trans. The crystal packing is stabilized by intermolecular C-HÁ Á Á interactions.

Experimental
To a stirred solution of methyl 2-(hydroxy(o-tolyl)methyl)acrylate (0.21 g, 1 mmol) in dichloromethane (10 mL), benzene (0.31 g, 4 mmol) was added at room temperature. After stirring for about 10 minutes at 273 K, catalytic amount of concentrated H 2 SO 4 was added drop wise. Then the reaction mixture was stirred at room temperature for 6 h. After completion of reaction, the mixture was poured into water and aqueous layer was extracted with ethyl acetate (3×10 ml).
The combined organic layer was washed with brine (20 mL), and dried over anhydrous Na 2 SO 4 . The crude product thus obtained was purified by column chromatography (2% EtOAc / hexanes) to provide the desired compound (E)-methyl-2benzyl-3-o-tolyl acrylate in 80% yield, as a colourless solid.

Refinement
All the hydrogen atoms of the compound are fixed geometrically and allowed to ride on their parent atoms with C-H distance in the range 0.93Å to 0.97Å and with U iso (H) = 1.5U eq (C) for CH 3 groups and U iso (H) = 1. groups.

Figure 1
The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at  The packing arrangement of the title compound viewed down c axis. The dashed line indicate C3-H3···Cg1 i intermolecular interaction. Cg1 is the centroid of the benzene ring (C13-C18). Symmetry code: (i) x+1, -y-1/2, z-3/2. where P = (F o 2 + 2F c 2 )/3 (Δ/σ) max < 0.001 Δρ max = 0.12 e Å −3 Δρ min = −0.20 e Å −3 Special details Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. 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 R-factors(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.