Methane, dichloromethoxy- → 2,7-Dimethoxy-1-naphthaldehyde

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Reaction Steps

The 2,7-dimethoxynaphthalene 2 (65 mmol; 12.26 g) is dissolved in 150 cm3 of anhydrous dichloromethane under an inert atmosphere. TiCl4 (91 mmol; 10cm3) is added by syringe, at 0° C., followed by dropwise addition, by means of a dropping funnel, of α,α-dichloromethyl methyl ether (99 mmol; 9 cm3) in solution in 40 cm3 of the same solvent. Stirring is continued at 0° C. for 1 h and then at room temperature for 4 h 30. The reaction medium is poured onto an ice/3N HCl mixture (250 cm3), stirred vigorously and then extracted with CH2Cl2. The organic phase is washed with water and then with saturated NaHCO3 solution. The organic phase is dried over MgSO4 and evaporated. The residue is taken up in ether, the solution is filtered and the filtrate is evaporated to dryness. 2,7-Dimethoxynaphthaldehyde 3 is isolated pure in the form of a beige-colored powder.

Provenance & Evidence