p-Toluenesulfonic acid → 2-Methyl-3H-cyclopenta[a]naphthalene

HRID 1266681Notes

Reaction equation

HRID 1266681 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4](S(O)(=O)=O)=[CH:3][CH:2]=1>O>[CH3:4][C:5]1[CH2:6][C:2]2[CH:3]=[CH:4][C:5]3[CH:3]=[CH:2][CH:1]=[CH:11][C:6]=3[C:1]=2[CH:11]=1

Participants

3

Reactant 1

HCID 6101p-Toluenesulfonic acid

Product 1

HCID 6020252-Methyl-3H-cyclopenta[a]naphthalene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

p-Toluenesulfonic acid (50 mg) was added to the organic layer, and the reaction mixture was heated under reflux with water separation for 1 h. After cooling to room temperature the organic layer was washed with sodium bicarbonate (aqueous 2 wt %, 50 ml), dried over magnesium sulfate, and concentrated under reduced pressure. The yield of 2-methyl-3H-benz[e]indene was 4.1 g or 89%.

Workup

  1. temperaturethe reaction mixture was heated
  2. washwas washed with sodium bicarbonate (aqueous 2 wt %, 50 ml)
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-19aaf8e486644df6b67ee861747a8325
Source dataset
uspto-grants-2003_04
Patent number
US06548710B2

Reaction notes

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