Hydrogen Peroxide → Chalcone epoxide

HRID 442412

Reaction equation

HRID 442412 reaction equation
[CH:1](=[CH:8][C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:17]O.[OH-].[Na+]>CO>[C:2]1([C:1](=[O:17])[CH:8]2[O:10][CH:9]2[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 7189CinnamoylbenzeneHCID 14798Sodium Hydroxide

Product 1

HCID 92219Chalcone epoxide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mechanically stirred mixture of 83.2 g benzalacetophenone (0.3m), 1000 ml methanol and 120 ml 15% hydrogen peroxide was added 100 ml 2N sodium hydroxide solution, while maintaining the temperature below 30° by external cooling. After completed addition, the mixture was left standing at room temperature for 20 min. The crystalline precipitate was filtered off, washed with water and recrystallized from methanol. There were obtained 59.6 g 1,3-diphenyl-2,3-epoxy-1-propanone; m.p. 90° C.

Workup

  1. temperaturewhile maintaining the temperature below 30° by external cooling
  2. additionaddition
  3. waitthe mixture was left
  4. filtrationThe crystalline precipitate was filtered off
  5. washwashed with water
  6. customrecrystallized from methanol

Sources & evidence

ORD record
ord-8b5d335fc60f4e27ac7e20977def2d90
Source dataset
uspto-grants-1977_08
Patent number
US04045487

Linked notes

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