Benzyl Bromide → Methyl 4-(benzyloxy)-2-hydroxybenzoate

HRID 1292036Notes

Reaction equation

HRID 1292036 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]([OH:12])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C([O-])([O-])=O.[K+].[K+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CC(C)=O>[CH2:19]([O:12][C:10]1[CH:9]=[CH:8][C:3]([C:4]([O:6][CH3:7])=[O:5])=[C:2]([OH:1])[CH:11]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 16523Methyl 2,4-Dihydroxybenzoate

Product 1

HCID 225489Methyl 4-(benzyloxy)-2-hydroxybenzoate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a well-stirred, 0° C. solution of methyl 2,4-dihydroxybenzoate (50 g, 300 mmol) in acetone (1000 mL) was added K2CO3 (150 g, 1000 mmol) and benzyl bromide (39 mL, 330 mmol). The solution was allowed to warm to ambient temperature over 48 h. The mixture was filtered through celite and the filtrate solvent was removed under reduced pressure. The residue was dissolved in EtOAc (1000 mL) and washed with water (250 mL) and saturated aqueous NaHCO3 (500 mL). The EtOAc layer was dried (MgSO4), filtered, and the EtOAc was removed under reduced pressure. The residue was purified by pressurized silica gel column chromatography using 5:1 hexanes:EtOAc as eluant. Methyl 4-benzyloxy-2-hydroxybenzoate was obtained as a white powder.

Workup

  1. filtrationThe mixture was filtered through celite
  2. customthe filtrate solvent was removed under reduced pressure
  3. dissolutionThe residue was dissolved in EtOAc (1000 mL)
  4. washwashed with water (250 mL) and saturated aqueous NaHCO3 (500 mL)
  5. dry with materialThe EtOAc layer was dried (MgSO4)
  6. filtrationfiltered
  7. customthe EtOAc was removed under reduced pressure
  8. customThe residue was purified by pressurized silica gel column chromatography

Sources & evidence

ORD record
ord-6ce137e333ec489d95f6c398d18e0fa5
Source dataset
uspto-grants-1998_05
Patent number
US05756497

Reaction notes

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