Water → 6,7-Dihydro-5H-benzocycloheptene

HRID 2271087Notes

Reaction equation

HRID 2271087 reaction equation
O.[C:2]1([CH3:12])[CH:7]=[CH:6][C:5](S(O)(=O)=O)=[CH:4][CH:3]=1.O>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH:6]1[C:7]2[CH:7]=[CH:2][CH2:3][CH2:4][CH2:12][C:2]=2[CH:3]=[CH:4][CH:5]=1

Participants

5

Reactant 2

HCID 962WaterHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 5822646,7-Dihydro-5H-benzocyclohepteneYield 1,773.9%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of this compound (7.00 g, 43.2 mmol) and para-toluenesulfonic acid monohydrate (0.82 g, 4.3 mmol) in toluene (100 ml) was refluxed for 1 hour with the azeotropic removal of water. The resulting solution was diluted with ethyl acetate, then washed with saturated sodium hydrogen carbonate solution, dried over MgSO4, filtered and evaporated to give 6,7-dihydro-5H-benzocycloheptene as a brown liquid (5.5 g, 88% yield).

Workup

  1. washwashed with saturated sodium hydrogen carbonate solution
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-ab771e62d1804ed59ff9d65a13dce68e
Source dataset
uspto-grants-2001_12
Patent number
US06333349B1

Reaction notes

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