Hydroquinone → HCID 10942603, compound

HRID 868277Notes

Reaction equation

HRID 868277 reaction equation
[C:1]1([CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)[OH:2].C(=O)([O-])[O-].[K+].[K+].[CH2:15](Br)[C:16]#[CH:17]>CC(C)=O>[CH2:17]([O:2][C:1]1[CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)[C:16]#[CH:15]

Participants

5

Reactant 3

HCID 785HydroquinoneHCID 7842Propargyl bromideHCID 11430Potassium Carbonate

Product 1

HCID 10942603HCID 10942603, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Hydroquinone (49.6 g; 450 mM) was dissolved in 700 ml of anhydrous acetone in a two liter, 3-necked, round bottom flask equipped with reflux condensor, air stirrer and nitrogen bubbler. Potassium carbonate (65.6 g; 460 mM) was ground finely and then added to the reaction followed by propargylbromide (53.6 g; 450 mM). The reaction was heated at reflux for three days, cooled to room temperature, filtered and the solvent removed. The residue was taken up in ether and extracted three times with 2.5N aqueous sodium hydroxide. The basic layers were acidified with concentrated hydrochloric acid while adding ice and extracted twice with ether. The combined ethereal layers were dried over magnesium sulfate, charcoal was added, and the mixture was filtered through celite. The solvent was removed in vacuo and the remaining dark brown sludge was purified by chromatography in two portions on a Waters Prep 500 equipped with two silica gel cartridges and eluted with 20% ethyl acetate in hexane after injecting in ether solution. This produced 21.4 g (64% of theory) of the desired p-propargyloxyphenol.

Workup

  1. custom3-necked, round bottom flask equipped
  2. temperaturewith reflux condensor, air stirrer and nitrogen bubbler
  3. additionadded to the reaction
  4. temperatureThe reaction was heated
  5. temperatureat reflux for three days
  6. filtrationfiltered
  7. customthe solvent removed
  8. extractionextracted three times with 2.5N aqueous sodium hydroxide
  9. additionwhile adding ice
  10. extractionextracted twice with ether
  11. dry with materialThe combined ethereal layers were dried over magnesium sulfate, charcoal
  12. additionwas added
  13. filtrationthe mixture was filtered through celite
  14. customThe solvent was removed in vacuo
  15. customthe remaining dark brown sludge was purified by chromatography in two portions on a Waters Prep 500
  16. customequipped with two silica gel cartridges
  17. washeluted with 20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-90d4d61e18b244378a0e92cea163918f
Source dataset
uspto-grants-1988_10
Patent number
US04778818

Reaction notes

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