Guaiacol → Ethyl (2-methoxyphenoxy)acetate

HRID 1057938Notes

Reaction equation

HRID 1057938 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[OH:9].C(=O)([O-])[O-].[K+].[K+].Br[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19]>CC(C)=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[O:9][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19]

Participants

5

Reactant 3

HCID 460GuaiacolHCID 7748Ethyl bromoacetateHCID 11430Potassium Carbonate

Product 1

HCID 83114Ethyl (2-methoxyphenoxy)acetate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2-methoxyphenol (11.3 g), potassium carbonate (25 g), ethyl bromoacetate (12 ml), and acetone (113 ml) was heated under reflux for 4 hours. After cooling to the room temperature, the mixture was filtered and the solvent was distilled off under reduced pressure from the filtrate. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1) to give Compound IIbd-a (17 g, 91%) as a pale-yellow oily substance.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 4 hours
  3. filtrationthe mixture was filtered
  4. distillationthe solvent was distilled off under reduced pressure from the filtrate
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1)
  6. customto give Compound IIbd-a (17 g, 91%) as a pale-yellow oily substance

Sources & evidence

ORD record
ord-03b4c84422e74e7cae602fc469941ece
Source dataset
uspto-grants-2003_02
Patent number
US06514996B2

Reaction notes

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