Phenol → HCID 517982, compound

HRID 2296260Notes

Reaction equation

HRID 2296260 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O-]CC.[Na+].Br[CH2:13][CH2:14][CH:15]([CH3:17])[CH3:16]>C(O)C>[CH2:13]([O:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH2:14][CH:15]([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 996PhenolHCID 78911-Bromo-3-methylbutaneHCID 2723922Sodium ethoxide

Product 1

HCID 517982HCID 517982, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Phenol (0.5 mole) was added to a solution of sodium ethoxide in ethanol (2 N; 250 ml) and 1-bromo-3-methylbutane (0.5 mole) was added dropwise while stirring. The mixture was heated under reflux for three hours and most of the solvent was then distilled off. Water was added to the residue and the organic layer was separated, washed twice with 10% aqueous NaOH, water, dilute H2SO4 and water, and was then dried over MgSO4. It was distilled in vacuo to give the title compound, b.p. 89°-92° C. at 14 mm Hg pressure. The identity and purity was confirmed by thin layer chromatography (TLC) and NMR and IR spectroscopy.

Workup

  1. additionwas added dropwise
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for three hours and most of the solvent
  4. distillationwas then distilled off
  5. additionWater was added to the residue
  6. customthe organic layer was separated
  7. washwashed twice with 10% aqueous NaOH, water, dilute H2SO4 and water
  8. dry with materialwas then dried over MgSO4
  9. distillationIt was distilled in vacuo

Sources & evidence

ORD record
ord-4235267d688e4812a827a95c57145b96
Source dataset
uspto-grants-1984_01
Patent number
US04428889

Reaction notes

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