Hydroquinone → 4-(5-Trifluoromethyl-pyridin-2-yloxy)-phenol

Temperature

60 °C

p-dihydroxybenzene 12.1 g (0.11 mol), anhydrous potassium carbonate 15.2 g (0.11 mol) were added to 500 mL of three-necked flask with DMF (200 mL) in sequence, the reaction mixture was then heated to 60° C., forming pale yellow turbid liquid, a solution of 2-chloro-5-(trifluoromethyl)pyridine 18.2 g (0.1 mol) in DMF (50 mL) was added dropwise to the above solution, after completion of addition for 15 min, then the mixture was heated to 90° C. and stirred for another 4 hours at this temperature. The reaction was monitored by thin-layer chromatography (TLC). After the reaction was completed, the reaction mixture was cooled to room temperature, then poured into water (300 mL) and extracted with ethyl acetate (2×300 mL). The organic phases were combined, washed with brine (2×200 mL), dried over anhydrous magnesium sulfate, concentrated under reduced pressure and the residue was purified via silica gel column chromatography (Fluent: ethyl acetate/petroleum ether=1:8) to give the product (19.1 g) as a white solid in 75% yield.

1. customforming pale yellow turbid liquid
2. additionafter completion of addition for 15 min
3. temperaturethe mixture was heated to 90° C.
4. temperaturethe reaction mixture was cooled to room temperature
5. extractionextracted with ethyl acetate (2×300 mL)
6. washwashed with brine (2×200 mL)
7. dry with materialdried over anhydrous magnesium sulfate
8. concentrationconcentrated under reduced pressure
9. customthe residue was purified via silica gel column chromatography (Fluent: ethyl acetate/petroleum ether=1:8)

ORD record

ord-a8663f4876d248c8b376e715fb31cf12

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08969332B2