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

HRID 1276031Notes

Reaction equation

HRID 1276031 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-160223f060b543579cabd5571eadc4ed
Source dataset
uspto-grants-2000_12
Patent number
US06165777

Reaction notes

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