Ethanol → 5,8-Dimethoxy-1,4-dihydronaphthalene

Participants

Reaction Steps

A suspension of 63.18 g (0.39 mole) of Part (2) 5,8-dihydro-1,4-naphthalenediol in 300 ml of absolute ethanol was heated briefly until solution was achieved. To this hot stirred solution was added alternately in 5 portions a solution of 40 g (1 mole) of sodium hydroxide in 100 ml of water, and 120 g (89 ml=0.95 mole) of dimethyl sulfate. The heat evolved during the addition caused the solution to reflux. After the addition was complete (approx. 30 minutes), a solution of 10 g of sodium hydroxide in 20 ml of water was added and the mixture was heated overnight at 75°.

Provenance & Evidence