Salicylaldehyde → 2-(Methoxymethoxy)benzaldehyde

Participants

Reaction Steps

Into a solution of tert-butoxy potassium (30.0 g, 0.27 mol) in DMF (200 mL) was dropped a solution of 2-hydroxybenzaldehyde (30.0 g, 0.25 mol) in DMF (100 mL) at 0° C. followed by stirring at room temperature for 1 hour. After addition of DMF (200 mL) thereto, a solution of chloromethylmethyl ether (21 mL, 0.27 mol) in DMF (200 mL) was dropped thereinto at 0° C. following by stirring at room temperature for 20 hours. The reaction mixture was poured over ice water followed by extracting with diethyl ether. The organic layer was washed with a 10% aqueous sodium hydroxide and a saturated saline solution successively and then dried over anhydrous sodium sulfate. The solvent was evaporated therefrom in vacuo to give the title compound (32.6 g, 80%) as an oily substance.

Provenance & Evidence