Hydrogen Peroxide → 2-(4-Bromo-2-ethylphenyl)-4,6-diethyl-4,6-dimethyl-1,5-dioxaspiro[2.4]heptan-7-one

HRID 341671Notes

Reaction equation

HRID 341671 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[C:9]2[C:13]([CH2:15][CH3:16])([CH3:14])[O:12][C:11]([CH2:18][CH3:19])([CH3:17])[C:10]2=[O:20])=[C:4]([CH2:21][CH3:22])[CH:3]=1.[OH:23]O.[OH-].[Na+]>CO>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:9]3([C:10](=[O:20])[C:11]([CH2:18][CH3:19])([CH3:17])[O:12][C:13]3([CH2:15][CH3:16])[CH3:14])[O:23]2)=[C:4]([CH2:21][CH3:22])[CH:3]=1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 687328484-[1-(4-Bromo-2-ethylphenyl)methylidene]-2,5-diethyl-2,5-dimethyldihydrofuran-3-one

Product 1

HCID 595627242-(4-Bromo-2-ethylphenyl)-4,6-diethyl-4,6-dimethyl-1,5-dioxaspiro[2.4]heptan-7-oneYield 71.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-[1-(4-bromo-2-ethylphenyl)methylidene]-2,5-diethyl-2,5-dimethyldihydrofuran-3-one (20 g, 0.055 mol) in methanol (800 ml) is added a solution of 50% aqueous hydrogen peroxide (9.58 ml, 0.165 mol) and a solution of 2N aqueous sodium hydroxide (10.98 ml, 0.02 mol) at ambient temperature. The reaction mixture is stirred at ambient temperature for 12-15 hours. The reaction mixture is quenched with a solution of saturated aqueous sodium metabisulfite, evaporated under reduced pressure to remove most of the solvent and extracted with dichloromethane (3×100 ml). The organic phases are combined, washed with water, and dried over anhydrous sodium sulfate. The mixture is filtered, and the filtrate is evaporated under reduced pressure to give 2-(4-bromo-2-ethylphenyl)-4,6-diethyl-4,6-dimethyl-1,5-dioxaspiro[2.4]heptan-7-one (15 g), used without further purification in the next step.

Workup

  1. customat ambient temperature
  2. customThe reaction mixture is quenched with a solution of saturated aqueous sodium metabisulfite
  3. customevaporated under reduced pressure
  4. customto remove most of the solvent
  5. extractionextracted with dichloromethane (3×100 ml)
  6. washwashed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationThe mixture is filtered
  9. customthe filtrate is evaporated under reduced pressure

Sources & evidence

ORD record
ord-9280f2605ade4e9f925a9ef8f315dcdd
Source dataset
uspto-grants-2014_11
Patent number
US08895761B2

Reaction notes

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