Hydrogen Peroxide → 2-Benzylidene-1-tetralone oxide

反応式

[CH:1](=[C:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]1=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:19]O.[OH-].[Na+]>CO>[CH:1](=[C:8]1[CH2:17][CH2:16][C:15]23[O:19][CH:14]2[CH:13]=[CH:12][CH:11]=[C:10]3[C:9]1=[O:18])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

実験手順

Ten grams (0.043 mole) of 2-benzylidene-1-tetralone (prepared as described in U.S. Pat. No. 3,926,988) is dissolved in 650 ml of MeOH at 35°, stirred, and treated with 10.5 g (0.092 mole) of 30% H2O2, followed by 10.5 ml (0.042 mole) of 16% NaOH solution while maintaining the temperature at 35°-36°. After stirring for 4 hours at room temperature, the solution is concentrated to approximately 50 ml on a rotary evaporator (high vacuum, low heat), diluted with 250 ml of cold H2O (an oil separates), extracted with ether (200 ml; then 4×100 ml), the combined ether layers dried (MgSO4), and the solvent evaporated to give 11.0 g (100%) of a semi-crystalline residue. Crystallization (of 10.6 g) from 55 ml of (i-Pr)2O gives 8.3 g (80%) of colorless solid; m.p. 71°-73°. Lit m.p. 77°-77.5° [JACS, 79, 232 (1957)].