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 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