Dimethylformamide → 2-Methoxy-3-methylbenzoic acid

HRID 1632212Notes

Reaction equation

HRID 1632212 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:4]([C:5]([OH:7])=[O:6])[C:3]=1[OH:11].CI.[CH3:14]N(C)C=O.[OH-].[Na+]>[Ag]=O.C(O)C>[CH3:14][O:11][C:3]1[C:2]([CH3:1])=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=[O:6]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 67383-Methylsalicylic AcidHCID 14798Sodium Hydroxide

Product 1

HCID 9523962-Methoxy-3-methylbenzoic acid

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalystHCID 702EthanolSolvent

Procedure

A mixture of 7.1 g. (0.05 mole) of 3-methylsalicylic acid, 23.1 g. (0.1 mole) of silver oxide and 25 ml. of methyl iodide in 150 ml. of N,N-dimethylformamide was stirred at 25° C. for 16 hours, then filtered. The filtrate was evaporated to provide a residue which was hydrolyzed by heating at 50° C. in an equivolume mixture of ethanol and 6N sodium hydroxide solution. The resulting mixture was acidified and filtered. The filtrate was evaporated, and the residue dissolved in base and treated with decolorizing charcoal. Acidification provided white solid 2-methoxy-3-methylbenzoic acid, m.p. 70°-75° C.

Workup

  1. additionA mixture of 7.1 g
  2. filtrationfiltered
  3. customThe filtrate was evaporated
  4. customto provide a residue which
  5. filtrationfiltered
  6. customThe filtrate was evaporated
  7. dissolutionthe residue dissolved in base
  8. additiontreated with decolorizing charcoal

Sources & evidence

ORD record
ord-3738f3f8394e48ce80094f15873a27e9
Source dataset
uspto-grants-1984_10
Patent number
US04474792

Reaction notes

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