Acetic Acid → 3-(Methoxymethoxy)-4-methylbenzoic acid

HRID 2426116Notes

Reaction equation

HRID 2426116 reaction equation
C([O:3][C:4](=[O:16])[C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[C:7]([O:12][CH2:13][O:14][CH3:15])[CH:6]=1)C.C(O)(=O)C>C(O)C.O.[OH-].[Na+]>[CH3:15][O:14][CH2:13][O:12][C:7]1[CH:6]=[C:5]([CH:10]=[CH:9][C:8]=1[CH3:11])[C:4]([OH:16])=[O:3]

Participants

6

Reactant 2

HCID 176Acetic AcidHCID 59649720HCID 59649720, compound

Product 1

HCID 596497153-(Methoxymethoxy)-4-methylbenzoic acid

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

3-Methoxymethoxy-4-methyl-benzoic acid ethyl ester (4.5 g, 20 mmol) was dissolved in a mixture of ethanol (50 mL), water (20 mL) and 1 N aqueous sodium hydroxide solution (30 mL) and stirred at room temperature for 18 hours. The mixture was concentrated under reduced pressure to remove most of the ethanol. The resulting aqueous solution was acidified by adding acetic acid (2.5 g, 41.6 mmol). White precipitate was formed. After standing for another 30 minutes, the precipitate was collected by filtration, washed with water and dried to give crude 3-methoxymethoxy-4-methyl-benzoic acid as a white powder. (Yield 3.82 g, 97.0%).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customto remove most of the ethanol
  3. customWhite precipitate was formed
  4. waitAfter standing for another 30 minutes
  5. filtrationthe precipitate was collected by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-77705084cb9e46f2b7fafaa3c4693f70
Source dataset
uspto-grants-2011_06
Patent number
US07968554B2

Reaction notes

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