Tetrahydrofuran → 1-Fluorenemethanol

Participants

Reaction Steps

60 g (0.36 mol) of fluorine was dissolved in 1,500 mL of dehydrated THF. Thereafter, 225 mL of a butyllithium hexane solution (1.6 M) was slowly added dropwise thereto at 0° C. in an argon gas atmosphere. 12 g of p-formaldehyde was then added, followed by stirring at room temperature for 5 hours. After stirring, 600 mL of a saturated sodium bicarbonate water was added, the mixture was extracted with diethyl ether, and the organic layer was washed twice with saturated saline. After drying over anhydrous magnesium sulfate, the solvent was distilled off. The resulting solid in a paste form was recrystallized from a mixed solvent of hexane and ethanol to obtain 50 g of fluorenylmethanol in a white acicular crystal form. It was confirmed that the resulting compound had the aforementioned structure represented by the formula (5) by measuring with 1H-NMR. The melting point and the measurement result of 1H-NMR are shown below.

Provenance & Evidence