Catechol → 1,2-Bis(benzyloxy)benzene

HRID 1165461Notes

Reaction equation

HRID 1165461 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-50692369c07c4317ac108c710881daa4
Source dataset
uspto-grants-1990_03
Patent number
US04910198

Reaction notes

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