1-Indanone → 1-Phenyl-1H-indene

Participants

Reaction Steps

To a solution of 1-indanone (23.78 g, 0.18 mol) in 250 mL of ether at 0° C. was added dropwise over 30 min, 100 mL of phenyllithium in ether (1.8M in ether) and the mixture was allowed to warm to room temperature and stirred for 1 h. The reaction mixture was poured into a cold saturated ammonium chloride solution, extracted with ether (2×200 mL), and the combined organic layer was washed with brine and dried over sodium sulfate. The organic solvent was removed under reduced pressure, 70 mL of 20% sulfuric acid in acetic acid was added to the residue and stirred 2 min. To the above solution water (100 mL) and ether (3×200 mL) were added. The organic layer was washed with sodium bicarbonate solution, dried over sodium sulfate, filtered, and concentrated. Toluene (300 mL) was added to the residue and the mixture was distilled (azeotropic removal of acetic acid) to afford a brown oil. The brown oil was purified by chromatography (silica; (2:1 hexane/methylene chloride)) to afford 15.58 g (45.82%) of 1-phenyl-indene as a colorless oil. In addition 11 g of 1-phenyl-1-acetoxy-indane was isolated as a by-product.

Provenance & Evidence