P-Cresol → 1-methyl-4-(prop-2-yn-1-yloxy)benzene

HRID 1607802Notes

Reaction equation

HRID 1607802 reaction equation
[CH:1]1[C:6]([OH:7])=[CH:5][CH:4]=[C:3]([CH3:8])[CH:2]=1.[OH-].[Na+].[CH2:11](Br)[C:12]#[CH:13]>O>[CH3:8][C:3]1[CH:4]=[CH:5][C:6]([O:7][CH2:13][C:12]#[CH:11])=[CH:1][CH:2]=1

Participants

5

Reactant 3

HCID 2879P-CresolHCID 7842Propargyl bromideHCID 14798Sodium Hydroxide

Product 1

HCID 3265921-methyl-4-(prop-2-yn-1-yloxy)benzene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 10.8 g (0.1 mol) of p-cresol in 70 ml of absolute ethanol,there were added 4 g of sodium hydroxide. The reaction mixture was refluxeduntil complete dissolution and then treated with 16.36 g (0.1 mol) of propargyl bromide (80% in toluene). Reflux was resumed for 14 additional hours. The reaction mixture was then cooled, poured into water and extracted with hexane (3×100 ml). The combined organic extracts werewashed with 20% aqueous sodium hydroxide solution and water, dried over sodium sulfate and the solvent removed by evaporation. The residue was distilled at 102° C./15 mm to yield 3-(p-methylphenoxy)-1-propyne, identical to an authentic sample.

Workup

  1. dissolutioncomplete dissolution
  2. temperatureReflux
  3. temperatureThe reaction mixture was then cooled
  4. extractionextracted with hexane (3×100 ml)
  5. dry with materialdried over sodium sulfate
  6. customthe solvent removed by evaporation
  7. distillationThe residue was distilled at 102° C./15 mm

Sources & evidence

ORD record
ord-bb8cca65d7b244919b20bdced08ff215
Source dataset
uspto-grants-1989_09
Patent number
US04867915

Reaction notes

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