Potassium Iodide → Methyl 4-(benzyloxy)-2-hydroxybenzoate

HRID 644290Notes

Reaction equation

HRID 644290 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.[I-].[K+]>CN(C=O)C>[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

6

Reactant 4

HCID 4875Potassium IodideHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 16523Methyl 2,4-Dihydroxybenzoate

Product 1

HCID 225489Methyl 4-(benzyloxy)-2-hydroxybenzoateYield 61.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Methyl 2,4-dihydroxybenzoate (20.0 g, 0.119 mol) was dissolved in DMF (400 mL) and potassium carbonate (17.2 g, 0.125 mol) and benzyl bromide (21.4 g, 0.125 mol) were added using additional DMF (400 mL) to aid the transfer. Potassium iodide (3.0 g) was added, and the reaction was stirred at room temperature under nitrogen for 48 h. The DMF was removed in vacuo and the residue was dissolved in ethyl acetate, washed with water and brine, dried, and the solvent was removed in vacuo to give a white solid which was recrystallized from ethyl acetate:hexane to yield 17.9 g (61.1%) of a white solid.

Workup

  1. customThe DMF was removed in vacuo
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with water and brine
  4. customdried
  5. customthe solvent was removed in vacuo
  6. customto give a white solid which
  7. customwas recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-c824782cd18f413e950dda9b716d266c
Source dataset
uspto-grants-2010_04
Patent number
US07700628B2

Reaction notes

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