تفاعل #63937

معادلة التفاعل

6-methoxy-1-tetralone

sulfur

hydrogen sulfide

→

naphthol

المردود 34.0%

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe mixture was cooled
2. 2
   workup.DISTILLATIONsubjected to bulb-to-bulb distillation
3. 3
   workup.DISSOLUTIONThe distillate was dissolved in 300 ml of dichloromethane
4. 4
   استخلاصthe solution was extracted with 1.0N potassium hydroxide solution (3×150 ml)
5. 5
   درجة الحرارةcooled in ice
6. 6
   أخرىto precipitate the crude naphthol product as a gum

الإجراء التجريبي

A mixture of 50.0 g (0.28 mole) of 6-methoxy-1-tetralone and 9.2 g (0.29 mole) of elemental sulfur was stirred and heated at 250°-260° for three hours (until the evolution of hydrogen sulfide gas had ceased). The mixture was cooled and then subjected to bulb-to-bulb distillation. The distillate was dissolved in 300 ml of dichloromethane, and the solution was extracted with 1.0N potassium hydroxide solution (3×150 ml). The base extracts were combined, cooled in ice, and acidified with 10% hydrochloric acid to precipitate the crude naphthol product as a gum. Trituration of the gum with tert-butyl methyl ether yielded 16.8 g (34% yield) of the analytically pure naphthol, mp 84°-86° (a mp of 83°-84° is given by M. P. Sibi, J. W. Dankwardt, and V. Snieckus, J. Org. Chem., 51, 271 (1986)).

المصدر