Acetone → HCID 825700, compound

HRID 1747651Notes

Reaction equation

HRID 1747651 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2([CH3:12])[CH3:11])=[CH:4][CH:3]=1.CC(C)=[O:15].S([O-])([O-])(=O)=O.[Mg+2].[Mn]([O-])(=O)(=O)=O.[K+]>O>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5](=[CH:4][CH:3]=1)[C:6](=[O:15])[CH2:7][C:8]2([CH3:12])[CH3:11]

Participants

6

Reactant 4

HCID 180AcetoneHCID 24083Sulfuric acid magnesium salt (1:1)HCID 516875Potassium PermanganateHCID 58575472HCID 58575472, compound

Product 1

HCID 825700HCID 825700, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 6-chloro-1,1-dimethylindane (6.00 g, 0.0332 mol) in acetone (100 mL, 2 mol) was added 1.5 M of magnesium sulfate in water (30 mL) and potassium permanganate (12.3 g, 0.0780 mol). The reaction was stirred overnight, the resulting deposit was filtered, and the solution was concentrated to a reduced volume. The solution was extracted with EtOAc (3×100 ml) and the organic layer was concentrated. Purification by flash chromatography (10% EtOAc/hexanes) afforded the title compound (4.33 g, 67%) as a white solid.

Workup

  1. filtrationthe resulting deposit was filtered
  2. concentrationthe solution was concentrated to a reduced volume
  3. extractionThe solution was extracted with EtOAc (3×100 ml)
  4. concentrationthe organic layer was concentrated
  5. customPurification by flash chromatography (10% EtOAc/hexanes)

Sources & evidence

ORD record
ord-86b14723aebd4bc1b9648042e3790623
Source dataset
uspto-grants-2015_10
Patent number
US09150525B2

Reaction notes

Loading…