Hydrochloric Acid → HCID 20306115, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred, 5° C mixture of m-dimethoxybenzene 27.6g (0.20 mole), anhydrous stannic chloride 52.1g (0.20 mole) and 200 ml of methylene chloride which is constantly swept with nitrogen, is added dropwise, 1,2-epoxyhexane, 20.0g (0.20 mole) in 50 ml of methylene chloride. The exothermic reaction temperature is maintained at 3° C by the rate of addition. After the addition is complete, the reaction is stirred at 5° C for 30 minutes, at which time it is poured into iced concentrated hydrochloric acid. The layers are separated and the aqueous layer is extracted with methylene chloride. The combined organic layers are washed with water followed by 5% sodium bicarbonate solution and finally water. The last water wash is neutral to pH paper. The methylene chloride solvent is removed on a rotary evaporator at 40° C bath temperature. This residue is then fractionally distilled in vacuo. The third fraction, 140°-142° C/0.2 mm, is shown by nmr and ir to be the desired product. The yield is 25.32g (55%, theory).

Provenance & Evidence