Guaiacol → HCID 13424816, compound

HRID 654836Notes

Reaction equation

HRID 654836 reaction equation
[C:1]1([O:8][CH3:9])[C:2](=[CH:4][CH:5]=[CH:6][CH:7]=1)[OH:3].Br[CH:11]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:12]([O:14][CH2:15][CH3:16])=[O:13].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:9][O:8][C:1]1[CH:7]=[CH:6][CH:5]=[CH:4][C:2]=1[O:3][CH:11]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

5

Reactant 3

HCID 460GuaiacolHCID 11430Potassium CarbonateHCID 97780Ethyl bromophenylacetate

Product 1

HCID 13424816HCID 13424816, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 130 g (1.05 m) guaiacol, 243 g (1 M) ethyl α-bromophenylacetate, 150 g of potassium carbonate and 1.5 L of acetone was refluxed for 96 hours, cooled and filtered. The solvent was removed at reduced pressure and the residue dissolved in toluene. After washing with dilute sodium hydroxide, then water, the solvent was removed and the residue distilled. The fraction boiling at 158-163°/0.4 mm was collected, weight 263 g.

Workup

  1. temperaturewas refluxed for 96 hours
  2. temperaturecooled
  3. filtrationfiltered
  4. customThe solvent was removed at reduced pressure
  5. dissolutionthe residue dissolved in toluene
  6. washAfter washing with dilute sodium hydroxide
  7. customwater, the solvent was removed
  8. distillationthe residue distilled
  9. customThe fraction boiling at 158-163°/0.4 mm was collected

Sources & evidence

ORD record
ord-b7c66d92a4cb4644aa8738ef786e0b8a
Source dataset
uspto-grants-1992_07
Patent number
US05134154

Reaction notes

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