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

HRID 1445458Notes

Reaction equation

HRID 1445458 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([OH:12])[C:5](=[CH:10][CH:11]=1)[C:6]([O:8][CH3:9])=[O:7].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:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([OH:12])[CH:3]=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 4-hydroxysalicylate (20.0 g, 119 mmol) was dissolved in DMF (400 ml), then potassium carbonate (17.2 g, 125 mmol) and benzyl bromide (21.4 g, 125 mmol) were added, using additional DMF (400 ml) to aid the transfer. Potassium iodide (3.0 g) was added, and the reaction mixture was stirred at room temperature under nitrogen for 48 h. The DMF was removed in vacuo, the residue taken up in EtOAc, washed with water (3×), brine, and dried. The organic layer was concentrated in vacuo, and the crude product recrystallized from EtOAc:hexane to give 17.9 g (61.1%) of a white solid. A second recrystallization of material recovered from the filtrate yielded an additional 6.2 g (21.2%) of product.

Workup

  1. customThe DMF was removed in vacuo
  2. washwashed with water (3×), brine
  3. customdried
  4. concentrationThe organic layer was concentrated in vacuo
  5. customthe crude product recrystallized from EtOAc

Sources & evidence

ORD record
ord-facb64fb40464456845c0f595f4c3967
Source dataset
uspto-grants-2010_02
Patent number
US07666866B2

Reaction notes

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