Hydrogen Peroxide → HCID 19001658, compound

HRID 1195270Notes

Reaction equation

HRID 1195270 reaction equation
[CH2:1]1[O:12][C:11]2[CH:10]=[C:9]3[C:5]([CH:6]=[CH:7][CH2:8]3)=[CH:4][C:3]=2[O:2]1.[OH2:13].[OH-].[Na+].OO>O1CCCC1.C(OCC)(=O)C>[CH2:1]1[O:2][C:3]2[CH:4]=[C:5]3[C:9]([CH2:8][CH:7]([OH:13])[CH2:6]3)=[CH:10][C:11]=2[O:12]1

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 14798Sodium HydroxideHCID 190016832H,5H-Indeno[5,6-d][1,3]dioxole

Product 1

HCID 19001658HCID 19001658, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 9.0 g of 5,6-methylenedioxyindene in 23 ml of tetrahydrofuran was cooled to 0° C. in a nitrogen atmosphere. A solution of 2.2 ml of 10.0 M borane/methyl sulfide complex in 5 ml of tetrahydrofuran was added dropwise thereto. The temperature of the mixture was elevated from 0° C. to room temperature over 4 h and then 1.8 ml of water was added dropwise thereto. 7.4 ml of a 3 M aqueous sodium hydroxide solution and then 5.5 ml of a 35% aqueous hydrogen peroxide solution were added thereto under cooling with ice and the mixture was stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate, washed with an aqueous common salt solution and dried over magnesium sulfate. The solvent was distilled off and the residue was crystallized from ethyl acetate to obtain 6.4 g of the intended compound in the form of white crystals.

Workup

  1. temperatureunder cooling with ice
  2. washwashed with an aqueous common salt solution
  3. dry with materialdried over magnesium sulfate
  4. distillationThe solvent was distilled off
  5. customthe residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-537acc26f6614763a8212b6e55eee06b
Source dataset
uspto-grants-1992_05
Patent number
US05110956

Reaction notes

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