Potassium Hydroxide → 2-Methoxy-3-methylbenzoic acid

HRID 2186637

Reaction equation

HRID 2186637 reaction equation
[CH3:1][O:2][C:3]1[C:12]([CH3:13])=[CH:11][CH:10]=[CH:9][C:4]=1[C:5]([O:7]C)=[O:6].[OH-].[K+]>CO.O>[CH3:1][O:2][C:3]1[C:12]([CH3:13])=[CH:11][CH:10]=[CH:9][C:4]=1[C:5]([OH:7])=[O:6]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 13229229Methyl 2-methoxy-3-methylbenzoate

Product 1

HCID 9523962-Methoxy-3-methylbenzoic acidYield 95%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 2 (1.19 mol) in a mixture of methanol (2 L) and water (0.5 L), potassium hydroxide pellets (100 gram, 1.5 mol) were added under cooling. The mixture was refluxed overnight and evaporated to dryness. The residue was dissolved in water (0.5 L) and acidified with HCl 6N. The product precipitated and 189 g of product was collected as white crystals. Yield 95%. 1H NMR (500 MHz, CDCl3, 25° C.) δ: 2.234 (s, 3H, CH3), 3.717 (s, 3H, OCH3), 7.062 (t, J=7.5, 1H, ArH), 7.365 (d, J=7.5, 1H, ArH), 7.496 (d, J=7.5, 1H, ArH).

Workup

  1. additionwere added
  2. temperatureunder cooling
  3. temperatureThe mixture was refluxed overnight
  4. customevaporated to dryness
  5. dissolutionThe residue was dissolved in water (0.5 L)
  6. customThe product precipitated
  7. custom189 g of product was collected as white crystals

Sources & evidence

ORD record
ord-dbaf181f786043bd93d9666b8a8a3bf8
Source dataset
uspto-grants-2002_06
Patent number
US06406297B1

Linked notes

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