Resorcinol → Benzyl 3-hydroxyphenyl ether

HRID 2080058Notes

Reaction equation

HRID 2080058 reaction equation
[C:1]1([CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[CH:3]=1)[OH:2].C(=O)([O-])[O-].[K+].[K+].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(OCC)(=O)C>CN(C)C=O.O>[CH2:15]([O:2][C:1]1[CH:3]=[C:4]([OH:5])[CH:6]=[CH:7][CH:8]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 5054ResorcinolHCID 7498Benzyl BromideHCID 8857Ethyl AcetateHCID 11430Potassium Carbonate

Product 1

HCID 138048Benzyl 3-hydroxyphenyl etherYield 33%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of resorcinol (10 g, 90.8 mmol) in N,N-dimethylformamide (100 mL) was added potassium carbonate (12.6 g, 90.8 mmol) and benzyl bromide (10.8 mL, 90.8 mmol), and the mixture was stirred at 60° C. for 2 hours. The reaction mixture was allowed to room temperature, ethyl acetate and water were added for partitioning, the organic layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was evaporated, then, the residue was purified by silica gel column chromatography (hexane:ethyl acetate), and 3-benzyloxy-phenol (6.0 g, 33%) was obtained as a pale brown oil.

Workup

  1. customwas allowed to room temperature
  2. customfor partitioning
  3. washthe organic layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated
  6. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate)

Sources & evidence

ORD record
ord-6c3253dc5c324731a5b81f83c14817fc
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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