Dichloromethane → 6-Methylnaphthalen-2-ol
Reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](C)=[CH:8][CH:7]=[CH:6]2.B(Br)(Br)Br.Cl[CH2:19]Cl>>[CH3:19][C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[CH:4]=[C:3]([OH:2])[CH:12]=[CH:11]2Participants
4
Conditions
- Temperature
- -60 °C
Procedure
To a solution of 6-methoxy-1-methylnaphthalene (6.4 g) in dichloromethane (500 ml), cooled to -60° C., was added boron tribromide (45 ml of a 1M solution in dichloromethane). The resulting mixture was stirred at -60° C. for 3 hours. The reaction was quenched with water (500 ml) and extracted with dichloromethane (2×500 ml). The organic extracts were combined, dried (MgSO4) and evaporated to give a solid. Purification by flash column chromatography on silica, eluting with ethyl acetate/hexane (5:95 v/v) gave 6-methyl-2-naphthol (3.76 g) as a white solid. This was used without further characterisation.