Methane → HCID 19351205, compound

Temperature

0 °C

A solution of 9-fluorenecarboxylic acid (12 g, 57 mmol) in 250 ml of THF was cooled to 0° C. under an argon atmosphere and 2 equiv. (71.25 ml) of a 1.6M n-butyl lithium solution in hexane was added followed by the addition of n-propyl iodide (7.5 ml, 13.1 g, 77 mmol). The reaction mixture was stirred at 0° C. for 6 hrs. An additional 1 ml of n-propyl iodide was added and the reaction stirred for 4 hrs at 0° C. The reaction was quenched by adding 75 ml of water and the pH was adjusted to pH 1 with 3N HCl. The reaction mixture was extracted with hexane (3×200ml) and the hexane extract washed with water, brine and dried over anhy. sodium sulfate. The solvents were evaporated yielding the crude product as a yellow oil which was dissolved in ~250 ml of ethanol and heated at reflux with Darco G-60, filtered through Celite and concentrated to approximately one half of the original volume. Water was slowly added until the mixture became cloudy. The mixture was reheated and slowly allowed to cool to room temperature yielding 10.5 grams (73%) of title compound as colorless crystals.

1. stirringthe reaction stirred for 4 hrs at 0° C
2. customThe reaction was quenched
3. additionby adding 75 ml of water
4. extractionThe reaction mixture was extracted with hexane (3×200ml)
5. extractionthe hexane extract
6. washwashed with water, brine
7. customdried over anhy
8. customThe solvents were evaporated
9. customyielding the crude product as a yellow oil which
10. temperatureheated
11. filtrationfiltered through Celite
12. concentrationconcentrated to approximately one half of the original volume
13. additionWater was slowly added until the mixture
14. temperatureto cool to room temperature

ORD record

ord-79e789d28e0d4bd7b0bbefc64234ef87

Source dataset

uspto-grants-1998_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05739135