p-Toluenesulfonic acid → 1-Phenyl-cycloheptene

HRID 1182486Notes

Reaction equation

HRID 1182486 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4](S(O)(=O)=O)=[CH:3][CH:2]=1>C1C=CC=CC=1>[C:1]1([C:11]2[CH2:4][CH2:3][CH2:2][CH2:1][CH2:6][CH:5]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 1

HCID 6101p-Toluenesulfonic acid

Product 1

HCID 2781321-Phenyl-cyclohepteneYield 84%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

In a round bottom flask fitted with a Dean Stark and a condenser was added a solution of alcohol (obtained above) in benzene (90 mL) and a catalytic amount of p-toluenesulfonic acid. The reaction mixture was refluxed for 3 hours and then cooled to room temperature. The mixture was washed with water (30 mL), brine (30 mL), dried (MgSO4), and concentrated to afford the corresponding alkene 90 (3.1 g, 84% yield). 1H NMR (400 MHz, CDCl3: δ 7.70-7.35 (m, 9H), 6.15 (t, J=8.0 Hz, 1H), 2.75-2.68 (m, 2H), 2.43-2.35 (m, 2H), 1.80-1.60 (m, 6H).

Workup

  1. customIn a round bottom flask fitted with a Dean Stark and a condenser
  2. temperatureThe reaction mixture was refluxed for 3 hours
  3. washThe mixture was washed with water (30 mL), brine (30 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-338b5f02c66d449ca46872d84e0fafc0
Source dataset
uspto-grants-2007_10
Patent number
US07288567B2

Reaction notes

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