Hydrogen Sulfide → 1-Naphthol

반응식

CO[C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[CH2:8][CH2:7][CH2:6]2.[S].S>>[CH:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[OH:13])[CH:4]=1

참가 물질

반응물 3

HCID 402Hydrogen Sulfide

HCID 141126-Methoxy-alpha-tetralone

HCID 5362487Sulfur

생성물 1

HCID 70051-Naphthol수율 34%

실험 절차

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)).