Isopropanol → HCID 825700, compound

HRID 222199Notes

Reaction equation

HRID 222199 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.S([O-])([O-])(=O)=[O:14].[Mg+2].[Mn]([O-])(=O)(=O)=O.[K+].C(O)(C)C>CC(C)=O.O>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5](=[CH:4][CH:3]=1)[C:6](=[O:14])[CH2:7][C:8]2([CH3:12])[CH3:11]

Participants

7

Reactant 4

HCID 3776IsopropanolHCID 24083Sulfuric acid magnesium salt (1:1)HCID 516875Potassium PermanganateHCID 58575472HCID 58575472, compound

Product 1

HCID 825700HCID 825700, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Procedure

6-chloro-1,1-dimethylindane (2.19 g, 0.0121 mol) was dissolved in acetone (50 mL), and 1.41 M solution of magnesium sulfate in water (9.02 mL) was added, followed by potassium permanganate (3.83 g, 0.0242 mol). The mixture was stirred at room temperature overnight. 1:1 water:isopropanol was then added to the mixture and this was stirred for 1 hour. The mixture was then evaporated to an aqueous residue and ethyl acetate was added. The mixture was filtered, washing the collected solids with EtOAc, and the filtrates were separated. The organic phase was concentrated, and the residue was purified by silica gel chromatography, eluting with 20 to 100% dichloromethane in hexanes to yield the product, 1.25 g (46%). 1H-NMR (400 MHz, CDCl, δ) 7.62 (d, J=8.3 Hz, 1H), 7.47 (d, J=1.6 Hz, 1H), 7.34 (dd, J=1.8 Hz, 8.1 Hz, 1H), 2.60 (s, 2H), 1.42 (s, 6H).

Workup

  1. stirringthis was stirred for 1 hour
  2. customThe mixture was then evaporated to an aqueous residue and ethyl acetate
  3. additionwas added
  4. filtrationThe mixture was filtered
  5. washwashing the collected solids with EtOAc
  6. customthe filtrates were separated
  7. concentrationThe organic phase was concentrated
  8. customthe residue was purified by silica gel chromatography
  9. washeluting with 20 to 100% dichloromethane in hexanes
  10. customto yield the product, 1.25 g (46%)

Sources & evidence

ORD record
ord-1eb8539816ae49fe99dffff573b37fb4
Source dataset
uspto-grants-2012_06
Patent number
US08207177B2

Reaction notes

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