Boron tribromide → 6-Hydroxy-7-methyl-1,2,3,4-tetrahydronaphthalen-1-one
Reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[CH3:13])[C:9](=[O:14])[CH2:8][CH2:7][CH2:6]2.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[CH3:13])[C:9](=[O:14])[CH2:8][CH2:7][CH2:6]2Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of 2.79 g (14.7 mmol) of 6-methoxy-7-methyl-1,2,3,4-tetrahydro-1-naphthalenone in 150 mL of CH2Cl2 was cooled in ice and treated with 20 mL (0.22 mol) of BBr3. After stirring at 0° C. for 0.5 hour, the solution was stirred at room temperature overnight. The solution was poured into ice water and extracted with Et2O. The Et2O was extracted twice with 5% NaOH and the NaOH washed with Et2O. The NaOH solution was acidified to the Congo Red end point with dilute HCl, then extracted with Et2O. The Et2O was washed with saturated NaCl and dried over MgSO4. Removal of the solvent under reduced pressure left the crude product. This was taken up in acetone and treated with charcoal. Filtering through Celite and removal of the solvent under reduced pressure left 2.08 g (80.6% yield) of the product as a brown solid. The structure was confirmed by NMR and mass spectroscopy. MS m/z 177 (M+H+).
Workup
- stirringthe solution was stirred at room temperature overnight
- extractionextracted with Et2O
- extractionThe Et2O was extracted twice with 5% NaOH
- washthe NaOH washed with Et2O
- extractionextracted with Et2O
- washThe Et2O was washed with saturated NaCl
- dry with materialdried over MgSO4
- customRemoval of the solvent under reduced pressure
- waitleft the crude product
- additiontreated with charcoal
- filtrationFiltering through Celite and removal of the solvent under reduced pressure
Sources & evidence
- ORD record
- ord-16d086381411490bba836103bee8091d
- Source dataset
- uspto-grants-2001_07
- Patent number
- US06265422B1
Reaction notes
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