Hydrochloric Acid → HCID 22173403, compound

Participants

Reaction Conditions

Reaction Steps

94.37 g (0.40 mol) 1,4-Dibromobenzene and 106.7 g (0.80 mol) anhydrous aluminum trichloride were placed in a 1000 ml round bottom flask equipped with a mechanical stirrer. 62.72 g (0.60 mol) 2-Methyl-acryloyl chloride were added under heat evolution (50-55° C.). The mixture was heated, starting at 105° C. a strong gas evolution was observed and the temperature rose to 135° C. Heating of the now solid mass was continued for 3 h at 110° C. After cooling to room temperature 200 g ice was added very carefully, followed by the careful addition of 200 ml cone. HCl. The mixture was extracted three times with 250 ml dichloromethane each. The combined organic layers were washed with 250 ml water and 250 ml of a saturated sodium bicarbonate solution, dried over magnesium sulfate, and the solvent was removed in vacuo. Flash chromatography using silica and heptane/dichloromethane (1:2) yielded 19.3 g (63 mmol, 16%) of the desired indanone as a white solid. 1H-NMR (500 MHz, CDCl3): δ=7.67, 7.54 (2×d, 2H, aromatic), 3.30 (m, 1H, COCHCH3), 2.74-2.64 (m, 2H, benzylic), 1.30 (d, 3H, CH3) ppm.

Provenance & Evidence