Acetic Acid → 1-[4-Methoxy-3-(trifluoromethyl)phenyl]ethan-1-one

A solution 1-methoxy-2-(trifluoromethyl)benzene (3.52 g) was dissolved in glacial acetic acid (30 ml) and treated with boron trifluoride acetic acid complex (30 ml) and the resulting solution maintained at 55° for 48 hours. The solution was poured into dilute hydrochloric acid (100 ml) and ice (100 g) added and the mixture extracted with chloroform (2×200 ml). The combined organic extracts were washed with sodium bicarbonate solution (3×100 ml), then water (100 ml), dried and evaporated to dryness to give an oily black solid. This was chromatographed on silica (40 g) eluting with ether:light petroleum (bp.60°-80°) (1:4) to give a solid which was crystallised from light petroleum (bp.60°-80°) to give the title compound (0.3 g), m.p.56°-57°

1. additiontreated with boron trifluoride acetic acid complex (30 ml)
2. temperaturethe resulting solution maintained at 55° for 48 hours
3. additionadded
4. extractionthe mixture extracted with chloroform (2×200 ml)
5. washThe combined organic extracts were washed with sodium bicarbonate solution (3×100 ml)
6. dry with materialwater (100 ml), dried
7. customevaporated to dryness
8. customto give an oily black solid
9. customThis was chromatographed on silica (40 g)
10. washeluting with ether
11. customlight petroleum (bp.60°-80°) (1:4) to give a solid which
12. customwas crystallised from light petroleum (bp.60°-80°)

ORD record

ord-8c56b564b5034e3d91995f2ceea2aa5b

Source dataset

uspto-grants-1994_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05356893