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

HRID 1434874Notes

Reaction equation

HRID 1434874 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].[C:12]([O-])([O-])=O.[K+].[K+].CI.CN([CH:23]=[O:24])C>>[CH3:12][O:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:3]=1[C:4]([O:24][CH3:23])=[O:5]

Participants

5

Reactant 4

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

Product 1

HCID 7172021Methyl 2-methoxy-4-methylbenzoateYield 91%

Procedure

To a mixture of 2-hydroxy-4-methylbenzoic acid (30.43 g, 200 mmol), K2CO3 (62.19 g, 450 mmol) and DMF (600 mL) was added methyl iodide (28.01 mL, 450 mmol). The reaction was stirred for 18 h, poured into ice/water (1.2 L), and extracted with EtOAc (2×300 mL). The combined organic layer was washed with brine, satd NaHCO3 and dried (MgSO4). The resulting solution was concentrated and distilled to give the title compound as a pale yellow liquid (32.73 g, 91%, bp 120-4° C./1333 Pa, 10 mm).

Workup

  1. extractionextracted with EtOAc (2×300 mL)
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationThe resulting solution was concentrated
  5. distillationdistilled

Sources & evidence

ORD record
ord-cd18b7f558ec4f5992951c5585003c72
Source dataset
uspto-grants-2009_11
Patent number
US07615568B2

Reaction notes

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