Hydrochloric Acid → 2-Cyclopropyl-6-methylphenyl acetate

Participants

Reaction Steps

A 500 ml four-necked round-bottomed flask was equipped with a magnetic stirrer bar, a thermometer, a reflux condenser and a drying tube. Magnesium (2.50 g, 102.8 mmol) and anhydrous THF (30 ml) were added thereto under a nitrogen atmosphere. Iodine (63 mg) was added to the mixture and the mixture was stirred at room temperature for 30 minutes. Subsequently, 2-(1,3-dibromopropyl)-6-methylphenyl acetate (30.0 g, 85.7 mmol) and anhydrous THF (90 ml) were added to the mixture at 80° C. over 15 minutes. After the mixture was stirred at 80° C. for 30 minutes, the mixture was further stirred at room temperature for 1.5 hours. 1M Hydrochloric acid (100 ml) was added dropwise to the reaction mixture such that the temperature of the reaction mixture did not exceed 40° C. The mixture was diluted with water (100 ml) and extracted with a 10% ethyl acetate-90% hexane (V/V) solvent mixture (3×200 ml). The organic layer was combined and it was successively washed with water (2×200 ml) and a saturated aqueous NaCl solution (50 ml), followed by drying with anhydrous sodium sulfate (100 g). After the solid was removed by filtration, the filtrate was concentrated to obtain 18.5 g of 2-cyclopropyl-6-methylphenyl acetate as a brown gum.

Provenance & Evidence