Hydrogen Peroxide → 2-Benzylidene-1-tetralone oxide

HRID 46472Notes

Reaction equation

HRID 46472 reaction equation
[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

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 1111792-Benzylidene-3,4-dihydronaphthalen-1-one

Product 1

HCID 867366902-Benzylidene-1-tetralone oxideYield 102.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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)].

Workup

  1. temperaturewhile maintaining the temperature at 35°-36°
  2. stirringAfter stirring for 4 hours at room temperature
  3. concentrationthe solution is concentrated to approximately 50 ml on a rotary evaporator (high vacuum, low heat)
  4. additiondiluted with 250 ml of cold H2O (an oil separates),
  5. extractionextracted with ether (200 ml
  6. dry with materialthen 4×100 ml), the combined ether layers dried (MgSO4)
  7. customthe solvent evaporated

Sources & evidence

ORD record
ord-36b2780cf9654c4293ba313dfa5cbe67
Source dataset
uspto-grants-1979_11
Patent number
US04173634

Reaction notes

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