Propargyl bromide → 2-Propargyloxy-2-phenyl-3-butyne

HRID 52392

Reaction equation

HRID 52392 reaction equation
[CH2:1](Br)[C:2]#[CH:3].[C:5]1([C:11]([OH:15])([C:13]#[CH:14])[CH3:12])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[OH-].[Na+].S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.O>CCCCCC.O>[CH2:1]([O:15][C:11]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)([C:13]#[CH:14])[CH3:12])[C:2]#[CH:3]

Participants

7

Reactant 4

HCID 7842Propargyl bromideHCID 14798Sodium HydroxideHCID 920983-Hydroxy-3-phenyl-1-butyneHCID 86750630Tetrabutyl ammonium hydrogen sulfate water

Product 1

HCID 112523922-Propargyloxy-2-phenyl-3-butyneYield 65%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8058HexaneSolvent

Procedure

Propargyl bromide (22 g, 0.15 mol) was dissolved in 140 ml of n-hexane. This solution, 2-phenyl-3-butyne-2-ol (14.6 g, 0.1 mol), NaOH (60 g, 1.5 mol) and a catalytic amount of tetrabutyl ammonium hydrogen sulfate/water (120 ml) were mixed, reacted for 24 hours at an ambient temperature and refluxed for 30 minutes. After completion of the reaction, the mixture was cooled to an ambient temperature and water (100 ml) was added. The organic phase was extracted with 30 ml of n-hexane, three times. The extracted organic solvent was dried with anhydrous magnesium sulfate, filtered and evaporated to separate. b.p.: 61° C./0.5 mmHg; yield: 65%; MS: m/e 184 (parent), 129 (base).

Workup

  1. customreacted for 24 hours at an ambient temperature
  2. temperaturerefluxed for 30 minutes
  3. customAfter completion of the reaction
  4. extractionThe organic phase was extracted with 30 ml of n-hexane, three times
  5. dry with materialThe extracted organic solvent was dried with anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customto separate

Sources & evidence

ORD record
ord-0eda761b3ecf455a8a5934f3ae9aab88
Source dataset
uspto-grants-1997_04
Patent number
US05616669

Linked notes

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