Tetralin → 2,3-dihydro-2,4-dimethyl-3-phenyl-6-(1-buten-3-yl)-7-hydroxy-1H-inden-1-one

HRID 4995

Reaction equation

HRID 4995 reaction equation
[CH3:1][CH:2]1[CH:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:9]2[C:4](=[C:5]([O:19]CC=CC)[CH:6]=[CH:7][C:8]2([CH3:18])C)[C:3]1=[O:24].[CH2:25]1[C:34]2C(=CC=CC=2)C[CH2:27][CH2:26]1>>[CH3:1][CH:2]1[CH:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:9]2[C:4](=[C:5]([OH:19])[C:6]([CH:26]([CH3:27])[CH:25]=[CH2:34])=[CH:7][C:8]=2[CH3:18])[C:3]1=[O:24]

Participants

3

Reactant 2

HCID 8404TetralinHCID 678826742,3-dihydro-2,4-dimethyl-3-phenyl-4-methyl-7-crotyloxy-1H-inden-1-one

Product 1

HCID 148347322,3-dihydro-2,4-dimethyl-3-phenyl-6-(1-buten-3-yl)-7-hydroxy-1H-inden-1-one

Procedure

11 Grams of 2,3-dihydro-2,4-dimethyl-3-phenyl-4-methyl-7-crotyloxy-1H-inden-1-one was added to 55 ml of tetrahydronaphthalene and the mixture was heated and refluxed for 6 hours with stirring condition. After the reaction was completed, the reaction mixture was concentrated by removal of the solvent, and the residue thus obtained was purified by means of a silica gel column chromatography. 11.2 Grams of 2,3-dihydro-2, 4-dimethyl-3-phenyl-6-(1-buten-3-yl)-7-hydroxy-1H-inden-1-one was obtained as cis-trans mixture. Yellow oily substance.

Workup

  1. temperaturethe mixture was heated
  2. temperaturerefluxed for 6 hours
  3. concentrationthe reaction mixture was concentrated by removal of the solvent
  4. customthe residue thus obtained
  5. customwas purified by means of a silica gel column chromatography

Sources & evidence

ORD record
ord-6c48a288eea14ea8baf5587a401e78ea
Source dataset
uspto-grants-1993_09
Patent number
US05242919

Linked notes

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