Catechol → 1,2-Bis(benzyloxy)benzene

HRID 34286Notes

Reaction equation

HRID 34286 reaction equation
[C:1]1([C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)O)[OH:2].[CH2:9](Br)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[C:17]([O-:20])([O-])=O.[K+].[K+]>CN(C=O)C.CCOCC>[CH2:9]([O:2][C:1]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[O:20][CH2:17][C:1]1[CH:3]=[CH:5][CH:6]=[CH:7][CH:8]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 289CatecholHCID 7498Benzyl BromideHCID 11430Potassium Carbonate

Product 1

HCID 12470951,2-Bis(benzyloxy)benzeneYield 93%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of catechol (11.0 g, 0.10M), benzylbromide (25.0 ml, 0.21M) and finely powdered anhydrous K2CO3 (44.2 g, 0.32M) in DMF (60 ml) was stirred at room temperature under N2 for 72 hours. The mixture was then diluted with Et2O and filtered. The ether solution was washed with three portions of distilled water, one portion of saturated NaCl solution, dried (K2CO3) and concentrated in vacuo. The residue was recrystallized from hexane to give dibenzyloxybenzene (27.04 g, 93% yield) as white crystals, mp 58°-59° C. (literature: Page et al., J. Org. Chem. 27, 218 (1962), mp 58°-59° C.).

Workup

  1. filtrationfiltered
  2. washThe ether solution was washed with three portions of distilled water, one portion of saturated NaCl solution
  3. dry with materialdried (K2CO3)
  4. concentrationconcentrated in vacuo
  5. customThe residue was recrystallized from hexane

Sources & evidence

ORD record
ord-23dc90a19b1f4e4b84a75ac2f1b55b95
Source dataset
uspto-grants-1988_08
Patent number
US04761413

Reaction notes

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