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

HRID 1463837Notes

Reaction equation

HRID 1463837 reaction equation
CI.[C:3](=O)([O-])[O-].[K+].[K+].[OH:9][C:10]1[CH:18]=[C:17]([CH3:19])[CH:16]=[CH:15][C:11]=1[C:12](O)=[O:13].CN(C)[CH:22]=[O:23]>>[CH3:3][O:9][C:10]1[CH:18]=[C:17]([CH3:19])[CH:16]=[CH:15][C:11]=1[C:12]([O:23][CH3:22])=[O:13]

Participants

5

Reactant 4

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

Product 1

HCID 7172021Methyl 2-methoxy-4-methylbenzoate

Procedure

Methyl iodide (123 mL, 1.95 mole) was added to a stirred suspension of potassium carbonate (360.0 g, 2.60 mole) in a solution of 2-hydroxy-4-methylbenzoic acid (100.0 g, 0.651 mole) in dimethylformamide (1500 mL) at room temperature. After stirring overnight, the reaction mixture was poured onto ice water (1000 mL) and the aqueous mixture extracted several times with ethyl acetate. The organic layers were combined, dried (Na2SO4), and stripped in vacuo to give a brown oil. After passage over silica gel using 20% ethyl acetate/hexane as the eluent, there was obtained 116.7 g of the title compound as an oil which was a single spot on thin layer chromatography (Rf 0.35, 20% ethyl acetate/hexane). NMR (CDCl3, 300 MHz, ppm): 2.4 (s, 3H); 3.87 (s, 3H); 3.9 (s, 3H); 6.78 (s, 1H); 6.8 (d, 1 =J Hz, 1 h); 7.72 (d, J= 7 Hz, 1H).

Workup

  1. additionthe reaction mixture was poured onto ice water (1000 mL)
  2. extractionthe aqueous mixture extracted several times with ethyl acetate
  3. dry with materialdried (Na2SO4)
  4. customto give a brown oil

Sources & evidence

ORD record
ord-f7c612851faf4619a78cf231f0307a12
Source dataset
uspto-grants-1994_04
Patent number
US05302601

Reaction notes

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