Methanol → 4,5-Dimethyl-9H-fluorene

Participants

Reaction Steps

A mixture of 4,5-dimethylfluorenone (7.0 g, 32.8 mmol), methanol (100 mL), ethyl acetate (50 mL), acetic acid (20 mL) and palladium hydroxide (20% on carbon, water content 44.43%, 1.0 g) was hydrogenated in a shaker at 35-40psi of hydrogen for 3.5 hr. The reaction was monitored by TLC (silica, 10% ethyl acetate/hexane). The catalyst was filtered off and the solvent was removed in vacuum, the residue was diluted with water (150 mL). The product was extracted with ethyl acetate (3×50 mL) and dried over magnesium sulfate. Evaporation of the solvent afforded 5.8 g (91.2%) of 4,5-dimethylfluorene.

Provenance & Evidence