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 6 N 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 vacuo and the residue was purified by column chromatography on silica gel to give cyclopentenylbenzene (21.49 g, 149 mmol, 100% yield) as a colorless oil. LC-MS (M+H)+=145.1. 1H NMR (500 MHz, chloroform-d) 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. temperatureat reflux for 2 h
3. dissolutiondissolved
4. extractionThe product was extracted with ether
5. washThe combined etherial layers were washed with saturated sodium bicarbonate solution
6. dry with materialdried over anhydrous magnesium sulfate
7. filtrationfiltered
8. customThe solvent was removed in vacuo
9. customthe residue was purified by column chromatography on silica gel

ORD-Eintrag

ord-7dd1daa45bab4f48af1acd4a231361a0

Quelldatensatz

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08637523B2