p-Toluenesulfonic acid → 6,7-Dihydro-5H-benzocycloheptene

HRID 2417381Notes

Reaction equation

HRID 2417381 reaction equation
[CH:1]1[C:6]2[CH2:7][CH2:8][CH2:9][CH2:10][CH:11](O)[C:5]=2[CH:4]=[CH:3][CH:2]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH:4]1[C:5]2[CH:11]=[CH:10][CH2:9][CH2:8][CH2:7][C:6]=2[CH:1]=[CH:2][CH:3]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 371715H-Benzocyclohepten-5-ol, 6,7,8,9-tetrahydro-

Product 1

HCID 5822646,7-Dihydro-5H-benzocyclohepteneYield 90.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 1.6 g (10 mmol) of 6,7,8,9-Tetrahydro-5H-benzocyclohepten-5-ol in 75 mL of benzene was added p-toluene sulfonic acid (19 mg, 0.1 mmol). The mixture was refluxed overnight using Dean-Stark equipment. After removal of the solvent, the residue was repartitioned between ethyl acetate and water. The organic layers was washed with saturated sodium bicarbonate solution, water and brine and dried over sodium sulfate. Removal of the solvent gave 1.3 g (88%) of 6,7-Dihydro-5H-benzocycloheptene(compound 23,scheme 11).

Workup

  1. temperatureThe mixture was refluxed overnight
  2. customAfter removal of the solvent
  3. washThe organic layers was washed with saturated sodium bicarbonate solution, water and brine
  4. dry with materialdried over sodium sulfate
  5. customRemoval of the solvent

Sources & evidence

ORD record
ord-1e544f8f62e9490bb54bde175f574973
Source dataset
uspto-grants-2004_11
Patent number
US06825208B2

Reaction notes

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