3-Methyl-5-phenylpentanoic acid → 7-methyl-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-one
Reaction equation
[C:1]1([CH2:7][CH2:8][CH:9]([CH3:14])[CH2:10][C:11]([OH:13])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>O>[CH3:14][CH:9]1[CH2:8][CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][C:6]=2[C:11](=[O:13])[CH2:10]1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
5-Phenyl-3-methylpentanoic acid (0.10 g, 0.52 mmol) was added to polyphosphoric acid (7 g), and the resulting mixture was stirred at 70° C. for 1 hour. Water was added to the reaction mixture, followed by extraction with ethyl acetate, and the extract solution was washed with water, a saturated aqueous sodium hydrogencarbonate solution and a saturated aqueous sodium chloride solution, and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 0.07 g of 7-methyl-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-one.
Workup
- extractionfollowed by extraction with ethyl acetate
- washthe extract solution was washed with water
- dry with materiala saturated aqueous sodium hydrogencarbonate solution and a saturated aqueous sodium chloride solution, and then dried over anhydrous magnesium sulfate
- distillationThe solvent was distilled off under reduced pressure
Sources & evidence
- ORD record
- ord-9647835d2ccb4842b0fb6397b7964098
- Source dataset
- uspto-grants-2002_04
- Patent number
- US06369110B1
Reaction notes
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