Vanillin → 4-Ethoxy-3-methoxybenzaldehyde

Participants

Reaction Conditions

Reaction Steps

76 grams of 4-hydroxy-3-methoxybenzaldehyde (0.5 mol) and 500 mL of isopropanol are added into a four-necked flask and then stirred for 20 minutes, a constant pressure dropping funnel is used for slowly dropping 150 milliliters of aqueous solution of 6.5 grams of 18-crown-6 ether and 133 grams of sodium hydroxide, and stirring is performed for 30 minutes, the reaction system is heated to 60° C., at which 85 grams of bromethyl is dropped for reacting for 5 to 6 hours while TLC tracking is implemented, after the reaction ends, the reaction system is cooled (to 15° C.) and is added with 500 mL of water for stopped reaction, the product is extracted by ether (3×300 mL), organic phase is washed with water to be neutral, anhydrous MgSO4 is dried, ether is partially distilled, a large amount of petroleum ether is added to precipitate crude product, the crude product is subjected to recrystallization by ether/petroleum ether to obtain 83 grams of 4-ethoxy-3-methoxybenzaldehyde:, and the yield is 92%.

Provenance & Evidence