Dimethylformamide → Methyl 2-methoxy-3-methylbenzoate

HRID 1869445Notes

Reaction equation

HRID 1869445 reaction equation
[C:1](=[O:4])([O-])[O-:2].[K+].[K+].O[C:8]1[C:16](C)=[CH:15][CH:14]=[CH:13][C:9]=1[C:10](O)=O.[CH3:18]I.CN(C)[CH:22]=[O:23]>>[CH3:18][O:2][C:1](=[O:4])[C:16]1[CH:15]=[CH:14][CH:13]=[C:9]([CH3:10])[C:8]=1[O:23][CH3:22]

Participants

5

Reactant 4

HCID 6228Dimethylformamide2×HCID 6328Methyl iodideHCID 67383-Methylsalicylic AcidHCID 11430Potassium Carbonate

Product 1

HCID 13229229Methyl 2-methoxy-3-methylbenzoateYield 59.3%

Procedure

199.9 g (1.45 mol) of potassium carbonate is introduced into 1.5 1 of dimethylformamide. At room temperature, 100 g (657.29 mol) of 2-hydroxy-3-methylbenzoic acid, dissolved in 250 ml of dimethylformamide, is added in drops. After 30 minutes of stirring, 90 ml of methyl iodide is added in drops, and the batch is stirred overnight. The reaction mixture is added to ice water and extracted three times with methyl tert-butyl ether. The organic phases are washed with water and brine. After drying, the solvent is spun off, and the residue is chromatographed on silica gel (mobile solvent ethyl acetate/hexane). 70.21 g (59.3%) of the desired compound is isolated.

Workup

  1. additionis added in drops
  2. stirringthe batch is stirred overnight
  3. extractionextracted three times with methyl tert-butyl ether
  4. washThe organic phases are washed with water and brine
  5. customAfter drying
  6. customthe residue is chromatographed on silica gel (mobile solvent ethyl acetate/hexane)

Sources & evidence

ORD record
ord-e592de29152a4a62af76d0ee6855aa9e
Source dataset
uspto-grants-2009_12
Patent number
US07638515B2

Reaction notes

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