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

HRID 322942Notes

Reaction equation

HRID 322942 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].[CH2:13](Cl)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CC(C)=O>[CH2:13]([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:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 16523Methyl 2,4-Dihydroxybenzoate

Product 1

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

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 180AcetoneSolvent

Procedure

A mixture of methyl 2,4-dihydroxybenzoate (50 g), benzyl chloride (37 mL), tetrabutylammonium bromide (0.25 g), potassium carbonate (44.4 g) and potassium iodide (18.4 g) in acetone is stirred at reflux overnight. The reaction mixture is evaporated to dryness and the residue is partitioned between water (300 mL) and ethyl acetate (300 mL). The organic layer is washed with aqueous sodium hydrogen carbonate solution and water, dried and evaporated. Crystallisation of the residue from ethyl acetate gives methyl 4-benzyloxy-2-hydroxybenzoate (45.1 g), in the form of a white solid.

Workup

  1. temperatureat reflux overnight
  2. customThe reaction mixture is evaporated to dryness
  3. customthe residue is partitioned between water (300 mL) and ethyl acetate (300 mL)
  4. washThe organic layer is washed with aqueous sodium hydrogen carbonate solution and water
  5. customdried
  6. customevaporated
  7. customCrystallisation of the residue from ethyl acetate

Sources & evidence

ORD record
ord-27768e08189949a3b6e774ba9a50c964
Source dataset
uspto-grants-2001_04
Patent number
US06211234B1

Reaction notes

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