Methyl 4-(benzyloxy)-3-methoxybenzoate

In the title compound, C16H16O4, the aromatic rings are almost normal to one another, making a dihedral angle of 85.81 (10)°. In the crystal, molecules are linked by C—H⋯O hydrogen bonds, forming chains propagating along the b-axis direction. There are also C—H⋯π interactions present which link the chains, forming two-dimensional networks lying parallel to (102).

In the title compound, C 16 H 16 O 4 , the aromatic rings are almost normal to one another, making a dihedral angle of 85.81 (10) . In the crystal, molecules are linked by C-HÁ Á ÁO hydrogen bonds, forming chains propagating along the b-axis direction.
There are also C-HÁ Á Á interactions present which link the chains, forming two-dimensional networks lying parallel to (102).

Comment
The title compound is an important organic intermediate which has been used to synthesis the antineoplastic drug Cediranib. The drug has shown promising activity against diseases which include lung and breast cancer (Folkman, 1996).
The molecular structure of the title molecule is shown in Fig. 1. The bond lengths (Allen et al., 1987) and angles are within normal ranges. In the molecule the two aromatic rings (C1-C6) and (C8-C13) are almost normal to one another with a dihedral angle of 85.81 (10) °.
In the crystal, molecules are linked by C-H···O hydrogen bonds forming chains propagating along the b axis direction (Table 1 and Fig. 2). There are also C-H···π interactions present (Table 1) linking the chains to form two-dimensional networks lying parallel to (102).

Experimental
The title compound was prepared according to the procedure reported by Li & Zhang (2012). A solution of 4-(benzyloxy)-3-methoxybenzoic acid (5 g, 19.36 mmol) was added slowly to a solution of methanol and concentrated sulfuric acid (2 ml). After being stirred for 12 h at reflux, saturated sodium bicarbonate solution was added to adjust the pH to 7.
Dichloromethane was added, and the mixture was then filtered and the organic phase evaporated on a rotary evaporator and to obtain the title compound. Block-like colourless crystals were obtained by dissolving (0.5 g, 1.84 mmol) of the title compound in ethanol (25 ml) and evaporating the solvent slowly at room temperature for about 7 days.

Refinement
All the H atoms were positioned geometrically and constrained to ride on their parent atom: C-H = 0.93 -0.96 Å with U iso (H) = 1.5U eq (C-methyl) and = 1.2U eq (C) for other H atoms.  The molecular structure of the title molecule, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level.

Figure 2
A view of the crystal packing of the title compound. The C-H···O hydrogen bonds are shown by dashed lines (see Table   1 for details; H atoms not involved in hydrogen bonding have been omitted for clarity). 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.