Potassium Carbonate → HCID 22467437, compound

HRID 1597204Notes

Reaction equation

HRID 1597204 reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=1[O:13][CH3:14].[CH3:15][O:16][CH2:17][CH2:18]Br.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:14][O:13][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:2]=1[O:1][CH2:18][CH2:17][O:16][CH3:15])[C:6]([O:8][CH2:9][CH3:10])=[O:7]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12038Ethyl vanillateHCID 809722-Bromoethyl methyl ether

Product 1

HCID 22467437HCID 22467437, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of ethyl 4-hydroxy-3-methoxybenzoate (9.8 g, 50 mmol), 2-bromoethyl methyl ether (8.46 ml, 90 mmol) and potassium carbonate (12.42 g, 90 mmol) in acetone (60 ml) was heated at reflux for 30 hours. The mixture was allowed to cool and the solids removed by filtration. The volatiles were removed from the filtrate by evaporation and the residue triturated with hexane to give ethyl 3-methoxy-4-(2-methoxyethoxy)benzoate (11.3 g, 89%) as a white solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 30 hours
  3. temperatureto cool
  4. customthe solids removed by filtration
  5. customThe volatiles were removed from the filtrate by evaporation
  6. customthe residue triturated with hexane

Sources & evidence

ORD record
ord-0c2a0d30ca1b4c20a65cadbd4c078905
Source dataset
uspto-grants-2001_09
Patent number
US06294532B1

Reaction notes

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