Water → 4,7-dimethyl-1H-indene

HRID 1464349Notes

Reaction equation

HRID 1464349 reaction equation
[Na].[CH3:2][C:3](=O)[CH2:4][CH2:5][C:6](=O)[CH3:7].[CH:10]1[CH2:14][CH:13]=[CH:12][CH:11]=1.O>CO>[CH3:7][C:6]1[CH:5]=[CH:4][C:3]([CH3:2])=[C:10]2[C:11]=1[CH:12]=[CH:13][CH2:14]2

Participants

6

Reactant 4

HCID 962WaterHCID 7612CyclopentadieneHCID 80352,5-HexanedioneHCID 5360545Sodium

Product 1

HCID 814584,7-dimethyl-1H-indene

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

23 g (1.0 mol) of sodium were dissolved in portions in 250 ml of absolute methanol. A mixture of 45.6 g (0.40 mol) of 2,5-hexanedione and 39.7 g (0.60 mol) of cyclopentadiene was then added dropwise at 0° C. in the course of 1 hour. After the mixture had been stirred at room temperature for 1 hours, 50 ml of water were added and the mixture was extracted with about 2 1 of diethylether. The residue which remained after the solvent had been stripped off was chromatographed on 1.4 kg of silica gel 60. 38 g (65%) of 4,6-dimethylindene (yellowish oil) were eluted with hexane/methylene chloride (10:1).

Workup

  1. additionwas then added dropwise at 0° C. in the course of 1 hour
  2. extractionthe mixture was extracted with about 2 1 of diethylether
  3. customwas chromatographed on 1.4 kg of silica gel 60
  4. wash38 g (65%) of 4,6-dimethylindene (yellowish oil) were eluted with hexane/methylene chloride (10:1)

Sources & evidence

ORD record
ord-929d889d0fe348cdb8f4db2cf559f28c
Source dataset
uspto-grants-1994_04
Patent number
US05304614

Reaction notes

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