Methyl iodide → Methyl 3-hydroxy-5-methoxybenzoate

HRID 1534600Notes

Reaction equation

HRID 1534600 reaction equation
CI.[OH:3][C:4]1[CH:5]=[C:6]([CH:11]=[C:12]([OH:14])[CH:13]=1)[C:7]([O:9][CH3:10])=[O:8].[C:15](=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[OH:3][C:4]1[CH:5]=[C:6]([CH:11]=[C:12]([O:14][CH3:15])[CH:13]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 75076Methyl 3,5-Dihydroxybenzoate

Product 1

HCID 13941268Methyl 3-hydroxy-5-methoxybenzoateYield 31.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl iodide (36 ml) was added to a mixture of methyl 3,5-dihydroxybenzoate (104 g), potassium carbonate (79 g) and dimethylformamide (1200 ml) and the mixture was stirred at ambient temperature for 16 hours. The mixture was partitioned between water (2.5 litre) and petrol (b.p. 60°-80° C., 600 ml). The aqueous layer was washed with petrol (b.p. 60°-80° C., 600 ml) and then extracted with toluene (2×1 litre). The toluene extracts were combined, washed with water (4×800 ml), dried (MgSO4) and evaporated to give methyl 3-hydroxy-5-methoxybenzoate as an oil (33 g, 30%).

Workup

  1. customThe mixture was partitioned between water (2.5 litre) and petrol (b.p. 60°-80° C., 600 ml)
  2. washThe aqueous layer was washed with petrol (b.p. 60°-80° C., 600 ml)
  3. extractionextracted with toluene (2×1 litre)
  4. washwashed with water (4×800 ml)
  5. dry with materialdried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-58cec50b74944e72a9db89a198535aa8
Source dataset
uspto-grants-1992_02
Patent number
US05089513

Reaction notes

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