2-Hydroxy-p-toluic acid → Methyl 2-methoxy-4-methylbenzoate

HRID 1741833Notes

Reaction equation

HRID 1741833 reaction equation
[OH:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].IC.[C:14](=O)([O-])[O-].[K+].[K+].CN(C)[CH:22]=[O:23]>>[CH3:14][O:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:3]=1[C:4]([O:23][CH3:22])=[O:5]

Participants

5

Reactant 4

HCID 57882-Hydroxy-p-toluic acidHCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium Carbonate

Product 1

HCID 7172021Methyl 2-methoxy-4-methylbenzoate

Procedure

A mixture of 2-hydroxy-4-methylbenzoic acid (7.61 g), iodomethane (15.6 ml) and potassium carbonate (17.3 g) in N,N-dimethylformamide (100 ml) was stirred at room temperature for 5 hours. The reaction mixture was filtered and the filtrate was poured into a mixture of ethyl acetate and water. The organic layer was separated, washed with water and brine, dried over magnesium sulfate and concentrated. The residue was chromatographed on silica gel column eluting with a mixture of n-hexane and ethyl acetate (4:1) to give methyl 2-methoxy-4-methylbenzoate (7.99 g) as an oil.

Workup

  1. filtrationThe reaction mixture was filtered
  2. additionthe filtrate was poured into a mixture of ethyl acetate and water
  3. customThe organic layer was separated
  4. washwashed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was chromatographed on silica gel column
  8. washeluting with a mixture of n-hexane and ethyl acetate (4:1)

Sources & evidence

ORD record
ord-964beffb22bb47339b52f46d1768c2f2
Source dataset
uspto-grants-1994_08
Patent number
US05334716

Reaction notes

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