Hydrochloric Acid → 5,8-difluoro-4-methyl-3,4-dihydro-1(2H)-naphthalenone

Participants

Reaction Conditions

Reaction Steps

1,4-Difluorobenzene (22 ml, 210 mmol) was mixed with gamma-valerolactone (4 ml, 42 mmol) and AlCl3 (28 g, 210 mmol) was added by portions to the stirred reaction mixture. The reaction mixture was then refluxed at stirring for 16 h (oil bath 110° C.). The reaction mixture was cooled down (ice/brine bath) and ice/conc. HCl was added and stirred until homogeneous mixture was obtained. The reaction mixture was then extracted into methylene chloride, washed with water (4×10 ml) and sodium bicarbonate solution (3×100 ml). The organic extract was dried over Na2SO4. Concentration by rotary evaporation gave 6.7 g of product as yellow powder. Yield 81%.

Provenance & Evidence