Hydroquinone → 4-But-2-ynyloxy-phenol

HRID 2417252Notes

Reaction equation

HRID 2417252 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+].Br[CH2:16][C:17]#[C:18][CH3:19]>CC(C)=O>[CH2:16]([O:2][C:1]1[CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)[C:17]#[C:18][CH3:19]

Participants

5

Reactant 3

HCID 785HydroquinoneHCID 11430Potassium CarbonateHCID 27568621-Bromo-2-butyne

Product 1

HCID 226340454-But-2-ynyloxy-phenolYield 32.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
57.5 °C

Procedure

To a solution of 4.13 g (0.038 mol) of hydroquinone in 80 mL of acetone was added 5.19 g (0.375 mol) of potassium carbonate and 5.0 g (0.038 mol) of 1-bromo-2-butyne. The resulting mixture was heated at 55-60° C. for 8 h and then stirred overnight at room temperature. The reaction mixture was then poured onto ice and extracted with ether. The combined organics were washed with 1N sodium hydroxide solution. The combined aqueous layers were acidified with 1N HCl solution and extracted with dichloromethane. The dichloromethane layers were washed with water and brine, dried over Na2SO4, filtered through Magnesol® and concentrated in vacuo to provide 2.0 g of the phenol as a brown oil.

Workup

  1. additionThe reaction mixture was then poured onto ice
  2. extractionextracted with ether
  3. washThe combined organics were washed with 1N sodium hydroxide solution
  4. extractionextracted with dichloromethane
  5. washThe dichloromethane layers were washed with water and brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered through Magnesol®
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6fe9ccd1eab84accaf4ea728d1d033aa
Source dataset
uspto-grants-2004_11
Patent number
US06825354B2

Reaction notes

Loading…