Catechol → 1,2-Bis(benzyloxy)benzene

HRID 1655554Notes

Reaction equation

HRID 1655554 reaction equation
O[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[C:9](=[O:12])([O-])[O-].[K+].[K+].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CC(C)=O>[C:16]1([CH2:15][O:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[O:12][CH2:9][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 289CatecholHCID 7498Benzyl BromideHCID 11430Potassium Carbonate

Product 1

HCID 12470951,2-Bis(benzyloxy)benzene

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 1,2-dihydroxybenzene (60 g, 0.54 mol) in 240 mL acetone, potassium carbonate (220 g, 1.59 mol) was added. After heating to reflux, benzylbromide (256.6 g, 1.5 mol) was added dropwise. The mixture was heated to reflux overnight, cooled, and poured onto 1 liter ice-water. The resulting precipitate (title compound) was filtered off with suction, washed with water, and dried in vacuo.

Workup

  1. temperatureAfter heating
  2. temperatureto reflux
  3. temperatureThe mixture was heated
  4. temperatureto reflux overnight
  5. temperaturecooled
  6. filtrationThe resulting precipitate (title compound) was filtered off with suction
  7. washwashed with water
  8. customdried in vacuo

Sources & evidence

ORD record
ord-b35e9de077e74c0783a140718aec706b
Source dataset
uspto-grants-1993_10
Patent number
US05250691

Reaction notes

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