Ethanol → 4-(Trifluoromethyl)aniline

A mixture of 400 mg (1.4 mmol) of 4-triethylsiloxy-4-trifluoromethyl-2,5-cyclohexadien-1-one, 572 mg (4.2 mmol) of ethyl glycinate hydrochloride, 298 mg (3.6 mmol) of sodium bicarbonate, and 10 mL of 95% ethanol was heated to reflux for 6 hours, allowed to cool to room temperature, and poured into 25 mL of water. The resulting aqueous mixture was extracted with three 10 mL portions of dichloromethane. The organic layers were combined and extracted with six 5 mL portions of 1N HCl. Combination of the aqueous layers and treatment with solid sodium bicarbonate until neutral to pH paper gave a cloudy mixture that was extracted with three 10 mL portions of dichloromethane. The organic layers were combined, dried (MgSO4), and stripped to give a residue which was purified by PTLC (one 2 mm silica gel plate eluted with dichloromethane), affording 160 mg (73% yield) of 4-trifluoromethylaniline.

1. temperaturewas heated
2. temperatureto reflux for 6 hours
3. extractionThe resulting aqueous mixture was extracted with three 10 mL portions of dichloromethane
4. extractionextracted with six 5 mL portions of 1N HCl
5. customgave a cloudy mixture that
6. extractionwas extracted with three 10 mL portions of dichloromethane
7. dry with materialdried (MgSO4)
8. customto give a residue which
9. customwas purified by PTLC (one 2 mm silica gel plate eluted with dichloromethane)

ORD record

ord-591d9c6f577542c097ccde0547d4697a

Source dataset

uspto-grants-1989_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04804772