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

Temperature

-75 °C

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.

1. stirringAfter stirring for 2 h at −75° C.
2. stirringwith stirring at −75° C. over 30 min
3. stirringThe mixture was stirred for additional 30 min at room temperature
4. customquenched
5. additionby adding water
6. extractionThe resulting mixture was extracted with 2×300 mL of ethyl acetate
7. washThe combined organic layers was washed with H2O
8. dry with materialdried over Na2SO4
9. concentrationconcentrated under vacuum

ORD record

ord-d34453f080d1467dba9be134e61f3f45

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09168248B2