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

HRID 2216738Notes

Reaction equation

HRID 2216738 reaction equation
[CH3:1][CH:2]1[CH:14](O)[C:5]2=[C:6]3[C:11](=[CH:12][CH:13]=[C:4]2[CH2:3]1)[CH:10]=[CH:9][CH:8]=[CH:7]3.C1(C)C=CC(S(O)(=O)=O)=CC=1.C([O-])([O-])=O.[Na+].[Na+]>C1C=CC=CC=1>[CH3:1][C:2]1[CH2:3][C:4]2[C:5]([CH:14]=1)=[C:6]1[C:11](=[CH:12][CH:13]=2)[CH:10]=[CH:9][CH:8]=[CH:7]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 10340Sodium CarbonateHCID 108888861H-Benz[e]inden-1-ol, 2,3-dihydro-2-methyl-

Product 1

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

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 2-methyl-2,3-dihydro-1H-cyclopenta[a]naphthalen-1-ol (obtained as described above) and 1 g of p-toluenesulphonic acid in 200 mL of benzene was refluxed for 1 h. Then the reaction mixture was cooled to room temperature and treated with a saturated aqueous solution of Na2CO3. The organic phase was isolated, dried over MgSO4 and evaporated off to dryness. Yield 14.2 g (55% based on starting 2-methyl-2,3-dihydro-1H-cyclopenta[a]naphtalen-1-one).

Workup

  1. temperaturewas refluxed for 1 h
  2. customThe organic phase was isolated
  3. dry with materialdried over MgSO4
  4. customevaporated off to dryness

Sources & evidence

ORD record
ord-bbc6bd5c4a0b41ccb4ad3af6e3a7d712
Source dataset
uspto-grants-2006_09
Patent number
US07112638B2

Reaction notes

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