4-BENZYLOXY-2-METHOXYBENZALDEHYDE

To a solution of 4-hydroxy-2-methoxybenzaldehyde (3)(200 mg, 1.31 mmol) in DMF was added K2CO3 (543 mg, 3.93 mmol) under N2 atmosphere and mixturewas stirred at room temperature for 30 min. BnBr (0.312 mL, 2.62 mmol) was added to reaction mixtureand stirred for 1.5 h. After the completion of the reaction, the reaction mixture was diluted with EtOAcand washed with H2O. The organic phase were dried with Na2SO4 and concentrated in vacuo purified bycolumn chromatography on silica gel using (EtOAc/hexanes = 1/2) to afford aldehyde 3a (304 mg, 95.7percent).1H-NMR (CDCl3, 400 MHz) δ 7.81 (d, 1H, J = 8.6 Hz), 7.36 (m, 5H), 6.62 (dd, 1H, J = 8.7, 2.2 Hz), 6.54(d, 1H, J = 2.2 Hz), 5.14 (s, 2H), 3.89 (s, 3H).Step 1: Step 1 : 4-Benzyloxy-2-methoxy-benzaldehydestep2 ~OMeBnO OMe~OMeHO)lAOMe4-Hydroxy-2-methoxybenzaldehyde (2.0 g, 13.15 mmol), benzyl bromide (3.14 ml, 26.3mmol) and potassium carbonate (3.63 g, 26.3 mmol) are combined in acetone ( 5 ml) andthe mixture is stirred for 4 hours. The mixture is concentrated under vacuum, suspended indichloromethane and washed with water. The organic phase is concentrated undervacuum and the residue purified by flash chromatography (1 0percent ethyl acetate incyclohexane) to give the title compound (yield 2.0 g).LC (LC METHOD 3): tR = 1.21 min; Mass spectrum (ESI+): m/z = 243 [M+Hr.Intermediate 99: 4-(Benzyloxy)-2-methoxybenzaldehydeTo a 100 mL RB flask fitted with magnetic stirrer was charged with 10 mL of acetonitrile. To the stirred solvent were added 4-(benzyloxy)-2-hydroxybenzaldehyde (1.0 g, 4.38 mmol), potassium carbonate (1.21 g, 8.76 mmol). The reaction mixture was brought to 0 °C, was added methyl iodide (1.135 g, 8.76 mmol) in acetonitrile (5 mL) drop wise and stirred at room temperature for 16 h. The reaction mixture was concentrated to distill off the solvent. The residue was extracted with ethyl acetate (50 mL). The organic layer was washed with water (40 mL) and saturated brine solution (40 mL). The organic layer was dried over anhydrous Na

Molecular Weight:242.27
XLogP3:2.8
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:5
Exact Mass:242.094294304
Monoisotopic Mass:242.094294304
Topological Polar Surface Area:35.5
Heavy Atom Count:18
Complexity:248
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes