Methanol → HCID 21105475, compound

HRID 2199871Notes

Reaction equation

HRID 2199871 reaction equation
[CH2:1]([O:5][C:6]1[C:15]([CH3:16])=[CH:14][C:9]([C:10]([O:12]C)=[O:11])=[CH:8][C:7]=1[CH3:17])[CH2:2][CH2:3][CH3:4].CO>[OH-].[K+]>[CH2:1]([O:5][C:6]1[C:7]([CH3:17])=[CH:8][C:9]([C:10]([OH:12])=[O:11])=[CH:14][C:15]=1[CH3:16])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 887MethanolHCID 89605979HCID 89605979, compound

Product 1

HCID 21105475HCID 21105475, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Procedure

A solution of methyl 4-butoxy-3,5-dimethylbenzoate represented by Formula 147 (2.1 g, 8.89 mmol) dissolved in potassium hydroxide (KOH, 44%, 5 mL) and methanol (40 mL) was agitated at 65° C. for 2 hours and cooled to room temperature, and the solvent was removed under reduced pressure. After dissolving the concentrate mixture in water then washing the mixture with ethylether (×3), 5N HCl aqueous solution was added to the obtained solution to reach pH 1. A precipitate generated during this process was obtained through filtration. After washing the obtained precipitate with water several times and drying the same, the dried precipitate was subjected to recrystallization in an ethyl acetate/hexane solvent. As a result, benzoic acid represented by Formula 145 was obtained as a desired product (907 mg, 46%). Analysis data of the product is provided as follows:

Workup

  1. customthe solvent was removed under reduced pressure
  2. dissolutionAfter dissolving the concentrate mixture in water
  3. washthen washing the mixture with ethylether (×3), 5N HCl aqueous solution
  4. additionwas added to the obtained solution
  5. customwas obtained through filtration
  6. washAfter washing the obtained precipitate with water several times
  7. customdrying the same, the dried precipitate
  8. customwas subjected to recrystallization in an ethyl acetate/hexane solvent

Sources & evidence

ORD record
ord-47b07a8e169f41658166a3d1584ee1d8
Source dataset
uspto-grants-2016_06
Patent number
US09359346B2

Reaction notes

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