6-Methoxy-2-Acetyl Naphthalene

Chemical Properties

Uses

Synthesis Reference(s)

General Description

Synthesis

92189-66-7

2700-47-2

Example 10 Synthesis of 1-(6-methoxynaphthalen-2-yl)propan-1-one: 29.3 g of 5-bromo-6-methoxy-2-propionyl naphthalene was dissolved in 100 ml of anhydrous dichloromethane and 20.8 ml of homotrimethylbenzene. Under strong stirring, 20 g of anhydrous aluminum chloride was added in batches to the reaction mixture that was cooled to -5 °C while the temperature was controlled below 20 °C. The reaction mixture was continued to be stirred at room temperature for 3 hours. Subsequently, the reaction mixture was slowly poured under strong stirring into a mixture consisting of 110 g of ice and 35 ml of a 35% (w/v) aqueous hydrochloric acid solution. After stirring for 15 minutes, the organic and aqueous layers were separated and the aqueous layer was discarded. The organic layer was sequentially washed twice with 50 ml of aqueous 6N hydrochloric acid solution and then with 50 ml of water. Next, 50 ml of water was added to the organic solution and the pH was adjusted with 30% (w/v) aqueous sodium hydroxide to 12. After discarding the aqueous phase, the organic phase was dried with anhydrous sodium sulfate and subsequently evaporated to dryness under vacuum. The residue was crystallized by n-heptane to give 20.2 g of 1-(6-methoxynaphthalen-2-yl)propan-1-one in 94.3% yield.

References