Phenol → (Prop-2-ynyloxy)benzene

HRID 628147Notes

Reaction equation

HRID 628147 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:8](Br)[C:9]#[CH:10].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[CH2:10]([O:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:9]#[CH:8]

Participants

6

Reactant 3

HCID 996PhenolHCID 7842Propargyl bromideHCID 11430Potassium Carbonate

Product 1

HCID 83613(Prop-2-ynyloxy)benzeneYield 84%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

Referring to FIG. 39, phenol (14.6 g, 0.155 mol), propargyl bromide (19 mL, 0.171 mol) and potassium carbonate (32.1 g, 0.232 mol) in DMF (100 mL) were heated at 85° C. overnight. The reaction was diluted with water and extracted with ether. The extract was washed with brine, dried (MgSO4) and evaporated. The residue was purified by Biotage flash column chromatography (10% EtOAc/Hep) to give product as an oil (17.2 g, 84%).

Workup

  1. extractionextracted with ether
  2. washThe extract was washed with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe residue was purified by Biotage flash column chromatography (10% EtOAc/Hep)

Sources & evidence

ORD record
ord-5faa30baecd344fa9c7401067b9eca6e
Source dataset
uspto-grants-2016_04
Patent number
US09309283B2

Reaction notes

Loading…