Hydrogen Peroxide → 2,3-Dihydro-2,3,3-trimethyl-1H-inden-1-one

HRID 495113Notes

Reaction equation

HRID 495113 reaction equation
[CH3:1][C:2]1([CH3:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[CH2:3]1.[CH2:13](B(CC)CC)C.CI.[OH-].[Na+].OO>C1COCC1.O>[CH3:1][C:2]1([CH3:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[CH:3]1[CH3:13]

Participants

8

Reactant 5

HCID 784Hydrogen PeroxideHCID 6328Methyl iodideHCID 7357TriethylboraneHCID 14798Sodium HydroxideHCID 3046283,3-Dimethyl-1-indanone

Product 1

HCID 101490362,3-Dihydro-2,3,3-trimethyl-1H-inden-1-oneYield 71.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

KH (32 g at 35% in mineral oil, 280 mmol, 1.4 equiv.) was suspended in THF (160 ml) and 3,3-dimethyl-1-indanone (as prepared as described above, 32 g, 200 mmol) in THF (150 mmol) was added. The green suspension was stirred for 1.5 h at RT, then triethylborane (1M solution in THF, 280 ml, 280 mmol, 1.4 equiv.) was added slowly. After 1 h stirring at RT methyl iodide (40 g, 280 mmol, 1.4 equiv.) was added and the suspension stirred for 48 h at RT. Treatment with H2O (240 ml), 10% aq. NaOH (240 ml) and 30% aq. H2O2-solution (240 ml) under occasional cooling was followed by extraction with MTBE. The organic layer was washed with brine, dried over MgSO4 and concentrated in a rotary evaporator. Bulb-to-bulb distillation (0.05 mbar/100° C.) yielded 24.8 g (71%) of product.

Workup

  1. additionwas added
  2. stirringthe suspension stirred for 48 h at RT
  3. extractionwas followed by extraction with MTBE
  4. washThe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in a rotary evaporator
  7. distillationdistillation (0.05 mbar/100° C.)

Sources & evidence

ORD record
ord-4908b7534f6d420e8c7620ac8b9aa710
Source dataset
uspto-grants-2009_05
Patent number
US07538243B2

Reaction notes

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