Hydrochloric Acid → Benzene, 1-cyclopenten-1-yl-

To a solution of 3.0 M solution of phenylmagnesium bromide in ether (49.7 mL, 149 mmol) was added THF (300 mL). To this solution cooled to 0° C. cyclopentanone (13.23 mL, 149 mmol) was added. The reaction mixture was stirred at room temperature for 30 min, then—at reflux for 2 h. Ice (20 g) was added, followed by 6N HCl, until the precipitate dissolved. The product was extracted with ether. The combined etherial layers were washed with saturated sodium bicarbonate solution, dried over anhydrous magnesium sulfate and filtered. The solvent was removed in vacuum and the residue was purified by column chromatography on silica gel to give cyclopentenylbenzene (21.49 g, 149 mmol, 100% yield) as colorless oil. LC-MS (M+H)+=145.1. 1H NMR (500 MHz, CDCl3) δ ppm 7.48 (2H, d, J=7.3 Hz), 7.35 (2H, t, J=7.8 Hz), 7.22-7.27 (1H, m), 6.22 (1H, t, J=2.1 Hz), 2.70-2.80 (2H, m), 2.52-2.64 (2H, m), 2.01-2.12 (2H, m).

1. additionwas added
2. dissolutiondissolved
3. extractionThe product was extracted with ether
4. washThe combined etherial layers were washed with saturated sodium bicarbonate solution
5. dry with materialdried over anhydrous magnesium sulfate
6. filtrationfiltered
7. customThe solvent was removed in vacuum
8. customthe residue was purified by column chromatography on silica gel

ORD record

ord-fa36e42af60e4947921e5a25b5cf4d1c

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08710061B2