Methyl Salicylate → 2-Isopropoxybenzoic acid

HRID 49946

Reaction equation

HRID 49946 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH:7](Br)([CH3:9])[CH3:8].[C:11]([O:20]C)(=[O:19])[C:12]1[C:13](=[CH:15][CH:16]=[CH:17][CH:18]=1)[OH:14].[OH-].[Na+]>C(O)C.CN(C)C=O>[CH:7]([O:14][C:13]1[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=1[C:11]([OH:20])=[O:19])([CH3:9])[CH3:8]

Participants

7

Reactant 4

HCID 4133Methyl SalicylateHCID 63582-BromopropaneHCID 11430Potassium CarbonateHCID 14798Sodium Hydroxide

Product 1

HCID 123576742-Isopropoxybenzoic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

5.00 g (36.2 mmol) of potassium carbonate and 3.27 g (26.6 mmol) of isopropyl bromide were added to a mixture of 2.00 g (13.2 mmol) of methyl salicylate and 10 ml of dimethylformamide, and they were stirred at room temperature overnight and then at 70° C. for 4 hours. 12.0 ml (36 mmol) of 3 M aqueous sodium hydroxide solution and 6.0 ml of ethanol were added to the reaction mixture, and they were stirred at 80° C. for 6 hours and then concentrated under reduced pressure. Water was added thereto. After washing with ethyl acetate, the aqueous layer was neutralized with hydrochloric acid. After the extraction with ethyl acetate, the extract was washed with water and saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain the title compound.

Workup

  1. waitat 70° C. for 4 hours
  2. stirringwere stirred at 80° C. for 6 hours
  3. concentrationconcentrated under reduced pressure
  4. additionWater was added
  5. washAfter washing with ethyl acetate
  6. extractionAfter the extraction with ethyl acetate
  7. washthe extract was washed with water and saturated aqueous sodium chloride solution
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-611e9242d9764af58057c91e52a12e2c
Source dataset
uspto-grants-2004_03
Patent number
US06710056B2

Linked notes

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