Hydrogen Peroxide → 1-Naphthalenecarboxylic acid, 5-bromo-6-methoxy-, methyl ester

HRID 36124Notes

Reaction equation

HRID 36124 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>CO>[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

HCID 784Hydrogen PeroxideHCID 24408BromineHCID 10921906Methyl 6-methoxy-1-naphthoate

Product 1

HCID 109352981-Naphthalenecarboxylic acid, 5-bromo-6-methoxy-, methyl esterYield 166.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

108 g (0.50 mol) of methyl 6-methoxy-1-naphthoate are dissolved in 2500 ml of methanol, and 30 g of 35% hydrogen peroxide solution are added. 42 g (0.26 mol) of bromine are then added dropwise at 35° C. in the course of 60 minutes. The mixture is subsequently heated at 70° C. When the reaction has ended, the mixture is concentrated in vacuo to a total volume of approximately 500 ml, allowed to cool to 20° C. and subjected to filtration with suction, and the filter cake is washed with methanol and water. Drying in vacuo at 60° C. gives 128.0 g of methyl 5-bromo-6-methoxy-1-naphthoate in the form of fine white needles.

Workup

  1. concentrationthe mixture is concentrated in vacuo to a total volume of approximately 500 ml
  2. temperatureto cool to 20° C.
  3. filtrationsubjected to filtration with suction
  4. washthe filter cake is washed with methanol and water
  5. customDrying in vacuo at 60° C.

Sources & evidence

ORD record
ord-addeb9e59a1e4386b3e98cdd42a9d142
Source dataset
uspto-grants-1995_05
Patent number
US05412150

Reaction notes

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