6-Methoxy-alpha-tetralone → 6-(benzyloxy)-3,4-dihydronaphthalen-1(2H)-one
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[CH2:8][CH2:7][CH2:6]2>Br>[CH2:1]([O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[CH2:8][CH2:7][CH2:6]2)[C:3]1[CH:4]=[CH:5][CH:10]=[CH:11][CH:12]=1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 120 °C
Procedure
A suspension of 6-methoxy-1-tetralone (99 g) in 48% hydrobromic acid (800 ml) was stirred overnight at 120° C. The reaction mixture was poured into ice water, the resulting solid was sequentially washed with water and hexane-diethyl ether system. To a solution of the resulting 6-hydroxy-3,4-dihydro-2H-naphthalen-1-one (76 g) in N,N-dimethylformamide (400 ml) were sequentially added potassium carbonate (76 g) and benzyl bromide (59 ml), and the solution was stirred for 4 hours at room temperature. The reaction mixture was poured into water, the resulting solid was sequentially washed with water and hexane-diethyl ether system to provide the title compound (110 g).
Workup
- washthe resulting solid was sequentially washed with water and hexane-diethyl ether system
- stirringthe solution was stirred for 4 hours at room temperature
- additionThe reaction mixture was poured into water
- washthe resulting solid was sequentially washed with water and hexane-diethyl ether system
Sources & evidence
- ORD record
- ord-c7e71b2f93e64b32964afe13fbf235c2
- Source dataset
- uspto-grants-2011_06
- Patent number
- US07960412B2
Reaction notes
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