Acetic Acid → 1-Methyl-8-chloro-2-tetralone

Participants

Reaction Steps

The dihydronaphthalene was dissolved in 30 ml of p-dioxane. To the solution were added 10 ml of methyl iodide, and the mixture was heated to reflux for 18 hours under nitrogen. To the reaction mixture then were added 25 ml of water and 1 ml of acetic acid, and the heating was continued for four hours. The reaction mixture then was cooled to room temperature, and the solvent was removed in vacuo. The resulting residue was suspended in water, and the aqueous mixture was extracted with ether. The organic extracts were combined, washed with saturated aqueous sodium chloride, dried over sodium sulfate, and evaporated in vacuo to give a dark oil. The oil was dissolved in ether and placed on a flash silica column. The column was eluted with a 1:1 mixture of hexane and ether containing a trace of ammonium hydroxide. The eluate was evaporated in vacuo to give 3.14 g of 1-methyl-8-chloro-2-tetralone as a mobile, orange liquid.

Provenance & Evidence