Hydrogen Peroxide → 1-Naphthalenecarboxylic acid, 5-bromo-6-methoxy-, methyl ester
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([C:13]([O:15][CH3:16])=[O:14])=[CH:8][CH:7]=[CH:6]2.OO.[Br:19]Br>C(O)(=O)C>[Br:19][C:4]1[C:3]([O:2][CH3:1])=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][CH:8]=[C:9]2[C:13]([O:15][CH3:16])=[O:14]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
108 g (0.50 mol) of methyl 6-methoxy-1-naphthoate are dissolved in 500 ml of acetic acid, and 30 g of 35% aqueous hydrogen peroxide solution are added. 42 g (0.26 mol) of bromine are then added dropwise at 35° C. in the course of 45 minutes. The mixture is subsequently heated at 90° C. When the reaction has ended, the mixture is allowed to cool to 20° C. and is subjected to filtration with suction, and the filter cake is washed with water. Drying in vacuo at 60° C. gives 136.1 g of methyl 5-bromo-6-methoxy-1-naphthoate in the form of fine white needles.
Workup
- temperatureto cool to 20° C.
- filtrationis subjected to filtration with suction
- washthe filter cake is washed with water
- customDrying in vacuo at 60° C.
Sources & evidence
- ORD record
- ord-4dad8a9fe83a452b8b273cd8d0a6b0c9
- Source dataset
- uspto-grants-1995_05
- Patent number
- US05412150
Reaction notes
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