Formaldehyde → 1-Fluorenemethanol

Participants

Reaction Steps

Fluorene 60 g (0.36 mol) was dissolved in dehydrated THF 1500 ml. Subsequently, butyl lithium-hexane solution 225 ml (1.6 M) was slowly dropped in at 0° C. under argon gas atmosphere. Next, paraformaldehyde 12 g was added and the mixture was agitated at a room temperature for 5 hours. After agitation, saturated sodium bicarbonate water 600 ml was added, and extracted with diethyl ether. An organic layer was washed twice with an aqueous saturated NaCl solution, and then the solvent was evaporated off after drying using anhydrous magnesium sulfate. The obtained pasty solid matter was refined by recrystallization with a mixed solvent of hexane and ethanol to obtain a white needle crystal 50 g of fluorenyl methanol. It was determined by measurement of 1H-NMR that the obtained compound had a structure illustrated in the above-described formula (6). The melting point and the measurement result of 1H-NMR will be shown in the following paragraph.

Provenance & Evidence