Formic Acid → HCID 24787891, compound

Temperature

40 °C

A mixture of 80% formic acid (100 mL, 2618 mmol) and 30% hydrogen peroxide (23 mL, 149 mmol) was warmed at 40° C. for 10 min. The resulting solution was carefully added to 1-cyclopentenyl-4-fluorobenzene (24.155 g, 149 mmol) while stirring. The two-phase system was initially stirred at room temperature. After a certain period of time, a spontaneous exothermic reaction took place, and the temperature rose to about 50° C. The reaction mixture was stirred at room temperature for 1 h. The reaction mixture was quenched by careful addition of a saturated sodium bicarbonate solution. Ether was added and the contents of the separatory funnel were vigorously shaken. The organic layer was separated and the aqueous layer was extracted with ether. The combined organic extracts were 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 2-(4-fluorophenyl)cyclopentanone (18.557 g, 104 mmol, 69.9% yield) as a colorless oil. LC-MS (M+H)+=177.2. 1H NMR (500 MHz, CDCl3) δ ppm 7.12-7.18 (2H, m), 6.98-7.04 (2H, m), 3.29 (1H, dd, J=11.6, 8.5 Hz), 2.42-2.54 (2H, m), 2.27 (1H, ddd, J=19.1, 10.5, 8.9 Hz), 2.12-2.20 (1H, m), 2.01-2.12 (1H, m), 1.87-1.99 (1H, m).

1. stirringThe two-phase system was initially stirred at room temperature
2. waitAfter a certain period of time
3. customa spontaneous exothermic reaction
4. customrose to about 50° C
5. stirringThe reaction mixture was stirred at room temperature for 1 h
6. customThe reaction mixture was quenched by careful addition of a saturated sodium bicarbonate solution
7. additionEther was added
8. stirringthe contents of the separatory funnel were vigorously shaken
9. customThe organic layer was separated
10. extractionthe aqueous layer was extracted with ether
11. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
12. filtrationfiltered
13. customThe solvent was removed in vacuo
14. customthe residue was purified by column chromatography on silica gel

ORD record

ord-0fd3dce843ae4186a8417de70ecfccd7

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08637523B2