Methyl 4-butoxy-3,5-dimethoxybenzoate → 4-Butoxy-3,5-dimethoxybenzoic acid

HRID 2199859Notes

Reaction equation

HRID 2199859 reaction equation
[CH2:1]([O:5][C:6]1[C:15]([O:16][CH3:17])=[CH:14][C:9]([C:10]([O:12]C)=[O:11])=[CH:8][C:7]=1[O:18][CH3:19])[CH2:2][CH2:3][CH3:4]>[OH-].[K+].CO>[CH2:1]([O:5][C:6]1[C:15]([O:16][CH3:17])=[CH:14][C:9]([C:10]([OH:12])=[O:11])=[CH:8][C:7]=1[O:18][CH3:19])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 1

HCID 10423152Methyl 4-butoxy-3,5-dimethoxybenzoate

Product 1

HCID 104450144-Butoxy-3,5-dimethoxybenzoic acidYield 78%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14797Potassium HydroxideSolvent

Procedure

After agitating a solution of methyl 4-n-butoxy-3,5-dimethoxybenzoate represented by Formula 92 (5.83 g, 21.74 mmol) dissolved in a potassium hydroxide solution (KOH, 44%, 10 mL) and methanol (120 mL) at 65° C. for 2 hours, the prepared solution was cooled to room temperature and the solvent was removed under reduced pressure. The concentrate mixture was dissolved again in water and washed with ethylether (×3). Then, a 5N-hydrochloric acid solution was added to the above prepared solution to reach pH 1, and a precipitate generated during this process was obtained through filtration. The obtained precipitate was washed using water several times and dried, followed by recrystallization using methanol (20 mL), resulting in benzoic acid represented by Formula 90 as a desired product (4.28 g, 78%). Analysis data of the product is provided as follows:

Workup

  1. customthe solvent was removed under reduced pressure
  2. dissolutionThe concentrate mixture was dissolved again in water
  3. washwashed with ethylether (×3)
  4. additionThen, a 5N-hydrochloric acid solution was added to the above prepared solution
  5. customwas obtained through filtration
  6. washThe obtained precipitate was washed
  7. customdried
  8. customfollowed by recrystallization
  9. customresulting in benzoic acid

Sources & evidence

ORD record
ord-02b81771735749d2bf60eb1493c88369
Source dataset
uspto-grants-2016_06
Patent number
US09359346B2

Reaction notes

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