Acetic Anhydride → 1-[2-Chloro-6-(methoxymethoxy)phenyl]ethanone

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-chloro-3-(methoxymethoxy)benzene (24 g, 136.74 mmol, 1.00 equiv, 98%) in THF (240 mL) was added TMP (21 g, 150.00 mmol, 1.10 equiv). To the above solution was added n-BuLi (61 mL, 1.10 equiv, 2.5 mol/L) dropwise with stirring at −75° C. over 30 min. After stirring for 2 h at −75° C., the resulting mixture was reacted with Ac2O (15.5 g, 148.92 mmol, 1.10 equiv, 98%) via dropwise addition with stirring at −75° C. over 30 min. The mixture was stirred for additional 30 min at room temperature, and then quenched by adding water. The resulting mixture was extracted with 2×300 mL of ethyl acetate. The combined organic layers was washed with H2O, dried over Na2SO4 and concentrated under vacuum to give 1-(2-chloro-6-(methoxymethoxy)phenyl)-ethanone as a yellow oil.

Provenance & Evidence