4'-Hydroxyacetophenone → 1-(4-(Ethoxymethoxy)phenyl)ethanone

Participants

Reaction Steps

In a 300 milliliter, three-necked oven-dried round bottom flask equipped with a magnetic stirrer, 25 grams (0.18 mole) of 1-(4-hydroxyphenyl)ethanone and 38.6 grams (0.27 mole) of potassium carbonate (K2CO3) were suspended in 200 milliliters of acetone and the mixture was stirred at room temperature for 1 hour, forming a thick slurry. 18.6 grams (0.198 mole) of (chloromethoxy)ethane was slowly added to the reaction mixture using a dropping funnel over a period of one hour and the reaction refluxed overnight for another 12 hours until completion was ascertained by TLC analysis (1:99 methanol/chloroform). The reaction was quenched by pouring the mixture slowly into 400 milliliters of 0.01% hydrochloric acid (HCl) solution, and the product was extracted into 300 milliliters of ethyl acetate, and washed with brine then water to a neutral pH. The ethyl acetate extracts were then dried over sodium sulfate, filtered, and concentrated on a rotary evaporator affording 34.58 grams (˜99% yield) of 1-(4-(ethoxymethoxy)phenyl)ethanone as an oil. The product was used without further purification. 1H NMR (500 MHz, Acetone-d6): δ 7.94-7.91 (d, 2H, 8.5 Hz), 7.13-7.07 (d, 2H, 8 Hz), 5.31 (s, 2H), 3.702-3.67 (q, 2H), 2.49 (s, 3H), 1.16-1.11 (t, 3H).

Provenance & Evidence