Hydrogen Peroxide → 3'-Phenylspiro[indene-2,2'-oxirane]-1,3-dione

HRID 1859078

Reaction equation

HRID 1859078 reaction equation
[CH:1](=[C:8]1[C:16](=[O:17])[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+].O>CO>[C:2]1([CH:1]2[C:8]3([C:9](=[O:18])[C:10]4[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=4)[C:16]3=[O:17])[O:19]2)[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 14798Sodium HydroxideHCID 2378222-Benzylidene-1,3-indandione

Product 1

HCID 31422143'-Phenylspiro[indene-2,2'-oxirane]-1,3-dione

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
5 °C

Procedure

To a suspension of 2-benzylidene-1,3-indandione (20 g) in methanol (200 ml) was added 30% hydrogen peroxide (19 ml). The suspension was cooled to 5° C. and 1 N sodium hydroxide (2.1 ml) was added dropwise at such a rate as to keep the temperature below 15 ° C. After completed addition, stirring was continued at room temperature for 30 minutes. The mixture was then poured into water (1.2 L). The resulting crystalline precipitate was collected by filtration, washed on the filter with water (3×100 ml) and dried under high vacuum at room temperature for 24 hours, affording 3-phenylspiro[oxirane-2,2'-indan]-1',3'-dione as a yellow solid (17 g).

Workup

  1. customthe temperature below 15 ° C
  2. additionaddition
  3. filtrationThe resulting crystalline precipitate was collected by filtration
  4. washwashed on the
  5. filtrationfilter with water (3×100 ml)
  6. customdried under high vacuum at room temperature for 24 hours

Sources & evidence

ORD record
ord-f5e821a3172d4116a7e7d12c233b35ab
Source dataset
uspto-grants-2000_11
Patent number
US06153645

Linked notes

Loading…