Phenol → (Prop-2-ynyloxy)benzene

HRID 630614Notes

Reaction equation

HRID 630614 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 m 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-60aa108bf8b54fb287e30b028f963a81
Source dataset
uspto-grants-2016_04
Patent number
US09315542B2

Reaction notes

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