Reaktion #74750

Reaktionsgleichung

2-benzylidene-1-tetralone

H2O2

NaOH

→

semi-crystalline residue

Ausbeute 102.2%

2-Benzylidene-1-tetralone oxide

Ausbeute 102.2%

Lösungsmittel

MeOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwhile maintaining the temperature at 35°-36°
2. 2
   workup.STIRRINGAfter stirring for 4 hours at room temperature
3. 3
   Einengenthe solution is concentrated to approximately 50 ml on a rotary evaporator (high vacuum, low heat)
4. 4
   workup.ADDITIONdiluted with 250 ml of cold H2O (an oil separates),
5. 5
   Extraktionextracted with ether (200 ml
6. 6
   Trocknenthen 4×100 ml), the combined ether layers dried (MgSO4)
7. 7
   Sonstigethe solvent evaporated

Vorschrift

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)].

Quelle