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

Temperature

0 °C

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 H2O (200 mL). The organic solution was dried (Na2SO4) 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).

1. waitat room temperature for 2 h
2. customThe reaction was quenched with H2O (500 mL)
3. customThe organic solution was separated
4. washwashed with H2O (2×500 mL), 0.5 N NaOH (2×100 mL)
5. dry with materialThe organic solution was dried (Na2SO4)
6. concentrationconcentrated
7. filtrationThe resulting residue was purified by filtration through a pad of silica gel

ORD record

ord-ca2ea7aa7d104799bcd14d3dc93f50d2

Source dataset

uspto-grants-2009_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07511066B2