Acetone → 2,3-Dihydro-1H-indene-1,2-diol

HRID 2394225Notes

Reaction equation

HRID 2394225 reaction equation
[CH2:1]1C2[C:4](=[CH:5][CH:6]=CC=2)[CH:3]=[CH:2]1.[CH3:10][C:11]([CH3:13])=[O:12].C[N+]1([O-])CC[O:18]CC1.S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>O.C(Cl)(Cl)(Cl)Cl.[Os](=O)(=O)(=O)=O.C(O)(C)(C)C>[OH:12][CH:11]1[C:13]2[C:2](=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:1][CH:10]1[OH:18]

Participants

9

Reactant 4

HCID 180AcetoneHCID 7219IndeneHCID 82029Methyl morpholine oxideHCID 656671Sodium Pyrosulfite

Product 1

HCID 5211972,3-Dihydro-1H-indene-1,2-diolYield 97%

Reagents, catalysts & solvents 4

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent2×HCID 5943Carbon TetrachlorideSolventHCID 6386tert-ButanolSolvent

Procedure

To a stirred solution of indene (0.5 g, 4.3 m mol), in a mixture of water (2.5 cm3), acetone (5 cm3) and tert-butanol (1.5 cm3), was added 4-methylmorpholine-N-oxide (0.6 g, 5.9 mmol) and a solution of osmium tetroxide in carbon tetrachloride (0.005 g/0.5 cm3). After stirring the reaction mixture for three days, at ambient temperature, a saturated aqueous solution of sodium metabisulphite (0.5 cm3) was added and the stirring was continued for another hour. The reaction mixture was diluted with water (50 cm3), extracted with ethyl acetate (2×50 cm3) and dried (Na2SO4). Distillation of the solvent, from the organic extract, under reduced pressure, gave crude racemic (1R:2S/1S:2R) 1,2-dihydroxy-1,2-dihydroindene as off-white fluffy crystals (0.63 g, 97%) m.pt. 98°-100° C.

Workup

  1. waitthe stirring was continued for another hour
  2. extractionextracted with ethyl acetate (2×50 cm3)
  3. dry with materialdried (Na2SO4)
  4. distillationDistillation of the solvent

Sources & evidence

ORD record
ord-bd2dc7f0fdb147f8bccd23a2b5acb765
Source dataset
uspto-grants-1998_09
Patent number
US05811294

Reaction notes

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