Acetone → HCID 57554470, compound

HRID 551976Notes

Reaction equation

HRID 551976 reaction equation
Br[CH:2](Br)[C:3]1[CH:4]=[CH:5][C:6]2[C:11](=[O:12])[O:10][C:9]([CH3:14])([CH3:13])[O:8][C:7]=2[CH:15]=1.CC(C)=[O:19]>O.[N+]([O-])([O-])=O.[Ag+]>[CH3:13][C:9]1([CH3:14])[O:8][C:7]2[CH:15]=[C:3]([CH:2]=[O:19])[CH:4]=[CH:5][C:6]=2[C:11](=[O:12])[O:10]1

Participants

5

Reactant 2

HCID 180AcetoneHCID 24179774HCID 24179774, compound

Product 1

HCID 57554470HCID 57554470, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 962WaterSolvent

Procedure

To a solution of 7-(dibromomethyl)-2,2-dimethyl-4H-1,3-benzodioxin-4-one (6.0 g, 17 mmol) in acetone (20 mL) and water (40 mL) under nitrogen was added AgNO3 (6.0 g, 35 mmol). The reaction mixture was stirred at rt for 14 hours, then filtered through a pad of Celite. The solvents were removed under reduced pressure. The residue was purified by chromatography (pet ether/EtOAc 9/1) to give 2.0 g (57%) of the titled compound as a solid. TLC-Pet Ether/EtOAc (7/3): Rf=0.7.

Workup

  1. filtrationfiltered through a pad of Celite
  2. customThe solvents were removed under reduced pressure
  3. customThe residue was purified by chromatography (pet ether/EtOAc 9/1)

Sources & evidence

ORD record
ord-b7845f36d6594992b88e4e2c053e11a6
Source dataset
uspto-grants-2011_05
Patent number
US07947851B2

Reaction notes

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