Hydrochloric Acid → HCID 10910812, compound

Temperature

250 °C

To a 250 ml round bottom flask equipped with nitrogen inlet, thermometer, and reflux condenser was charged 3.5 g (0.0147 moles) of 5-(3-hydroxyphenyl)-3-phenyl-2-pyrazoline, and 2.2 g (0.1 moles) of powdered sodium hydroxide. The two solids were mixed thoroughly, then heated slowly to 250° C., under a rapid steam of nitrogen. The reaction mixture was heated continuously at 250° C. for a total of 2 hours, then cooled to ambient temperature. The resulting residue was the dissolved in 200 mls of water, then acidified to pH 2 with 1N aqueous hydrochloric acid. The acidic solution was extracted with 3×100 mls of ethyl ether, and the ether extract was washed with 2×100 mls of water, and 100 mls of saturated aqueous sodium chloride solution. The ether extract was the dried over anhydrous magnesium sulfate, filtered and concentrated to dryness under reduced pressure with a rotary evaporator at 45° C. The resulting crude product was chromatographed on silica gel with a 15% ethyl acetate, 85% hexane mobile phase. The pure fractions were combined and concentrated under reduced pressure on a rotary evaporator to afford 1.8 g of the title compound 1-(3-hydroxyphenyl)-2-phenyl-cyclopropane as a pale yellow liquid in a 58% yield. 1H NMR (CDCl3, tms=0 ppm) 1.4(t,2H); 2.2(m,2H); 5.5(s,1H); 6.5-6.8(m,3H); 3.1-3.4(m,6H).

1. customTo a 250 ml round bottom flask equipped with nitrogen inlet
2. temperaturethermometer, and reflux condenser
3. additionThe two solids were mixed thoroughly
4. temperatureThe reaction mixture was heated continuously at 250° C. for a total of 2 hours
5. temperaturecooled to ambient temperature
6. extractionThe acidic solution was extracted with 3×100 mls of ethyl ether
7. extractionthe ether extract
8. washwas washed with 2×100 mls of water, and 100 mls of saturated aqueous sodium chloride solution
9. extractionThe ether extract
10. dry with materialdried over anhydrous magnesium sulfate
11. filtrationfiltered
12. concentrationconcentrated to dryness under reduced pressure with a rotary evaporator at 45° C
13. customThe resulting crude product was chromatographed on silica gel with a 15% ethyl acetate, 85% hexane mobile phase
14. concentrationconcentrated under reduced pressure on a rotary evaporator

ORD record

ord-f5bb91cb87dd4687953af460b5fd04f6

Source dataset

uspto-grants-2000_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06022891