4-Ethoxy-3-methoxybenzaldehyde

In the title compound, C10H12O3, all non-H atoms are approximately coplanar, with an r.m.s. deviation of 0.046 Å. In the crystal, very weak C—H⋯O interactions link the molecules into sheets parallel to (101).

In the title compound, C 10 H 12 O 3 , all non-H atoms are approximately coplanar, with an r.m.s. deviation of 0.046 Å . In the crystal, very weak C-HÁ Á ÁO interactions link the molecules into sheets parallel to (101).

Comment
Dehydrozingerone derivatives belong to an important class of compounds, not only due to their different bioactivities (Tatsuzaki et al., 2006;Kubra et al., 2013), but also as the key substrates in synthesis of some heterocycles (Panda et al., 2008), particularly flavones (Mostahar et al., 2007). They can be synthesized by condensation of the corresponding aromatic aldehyde with acetone. Thus, starting substrate in synthesis of ethyl derivative of dehydrozingerone is 4-ethoxy-3-methoxybenzaldehyde (I), compound obtained by simple methylation of vanillin.
In the title structure, all non-hydrogen atoms are approximately coplanar with a mean deviation of 0.046 Å (Fig. 1). A somewhat higher displacement of 0.102 (2) Å has been observed for atom C9 belonging to ethoxy moiety. The dihedral angle between the best planes through the phenyl ring and the non-H atoms of ethoxy moiety is 8.1 (1)°. The aromatic C -C bond lengths are in the expected range of 1.368 (2)-1.411 (2) Å ( Table 2). The five C-O bonds have various lengths. The shortest length is found for the carbonyl C1-O1 = 1.204 (2) bond in accordance with the prevaling double bond character.

Experimental
Diethyl sulfate was dropped into a water solution of sodium hydroxide and vanillin. The reaction mixture was stirred overnight at 50°C and cooled at room temperature resulting firstly an oily product, which on standing gave crude crystal 4-ethoxy-3-methoxybenzaldehyde.
One gram of crude 4-ethoxy-3-methoxybenzaldehyde was stirred vigorously in 150 ml of boiling water, the hot mixture filtered of through a cotton pad. The obtained milky-white emulsion upon overnight cooling at room temperature gave crystal needles of 4-ethoxy-3-methoxybenzaldehyde.

Refinement
All H atoms were included in calculated positions and treated as riding with d(C-H) equal to: 0.96 Å (CH 3 ), 0.97 Å (CH 2 ) or 0.93 Å (aromatic CH) and U iso (H) equal to: 1.5 U eq (C) for CH 3 or 1.2 U eq (C) for CH 2 and CH.

Figure 1
The molecular structure of the title compound, with atom labels and 30% probability displacement ellipsoids for non-H atoms.

Figure 2
Three-dimensional layered structure of the title compound. All H atoms which are not involved in intermolecular interactions are omitted for clarity.