Chloromethyl Methyl Ether → 1-[3-(Methoxymethoxy)phenyl]ethan-1-one

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 3-hydroxyacetophenone (20.40 g, 150 mmol) in CH2Cl2 (450 mL) at 0° C. under N2 was added N,N-diisopropylethylamine (52.25 mL, 300 mmol) followed by methyl chloromethyl ether (MOM chloride) (13.67 mL, 180 mmol) over a period of 30 min. The reaction was stirred at 0° C. for 30 min and then at room temperature for 2 h. The reaction was quenched with H2O (500 mL). The organic solution was separated, washed with H2O (2×500 mL), 0.5 N NaOH (2×100 mL), and again with H1120 (200 mL). The organic solution was dried (Na2 SO4) and concentrated. The resulting residue was purified by filtration through a pad of silica gel using n-hexanes through 2-5% EtOAc/n-hexanes to give the desired product (17.30 g, 64%); TLC Rf: 0.45 (20% EtOAc/n-hexanes).

Provenance & Evidence