Dimethyl Sulfate → 5-Bromo-6-methoxy-2-naphthaldehyde

HRID 374870Notes

Reaction equation

HRID 374870 reaction equation
[Br:1][C:2]1[C:11]([OH:12])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH:13]=[O:14])=[CH:7]2.[C:15](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O>CC(C)=O>[Br:1][C:2]1[C:11]([O:12][CH3:15])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH:13]=[O:14])=[CH:7]2

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 189963195-Bromo-6-hydroxy-2-naphthaldehyde

Product 1

HCID 185053535-Bromo-6-methoxy-2-naphthaldehydeYield 96%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Step c) A mixture of 5-bromo-6-hydroxy-2-naphthaldehyde (34.0 g, 135.5 mmol), potassium carbonate (18.7 g, 135.5 mmol), dimethyl sulfate (12.8 mL, 135.5 mmol) and acetone (500 mL), was refluxed for 3 hours. The volatiles were removed in vacuo, and the residue was suspended in water. The precipitated solid was filtered and dried, to yield a yellow solid (34.5 g, 96% yield, m.p. 133°-135° C.).

Workup

  1. temperaturewas refluxed for 3 hours
  2. customThe volatiles were removed in vacuo
  3. filtrationThe precipitated solid was filtered
  4. customdried

Sources & evidence

ORD record
ord-14b266396bdb442a9c24c38b7460dc6f
Source dataset
uspto-grants-1996_01
Patent number
US05482968

Reaction notes

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