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

HRID 2081106Notes

Reaction equation

HRID 2081106 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.O.[OH-].[Na+].C(O)(=O)C>C(O)C>[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 4

HCID 176Acetic AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 59649720HCID 59649720, compound

Product 1

HCID 596497153-(Methoxymethoxy)-4-methylbenzoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-methoxymethoxy-4-methyl-benzoic acid ethyl ester (4.5 g, 20 mmol) (from Example 3 supra) in a mixture of ethanol (50 mL), water (20 mL) and 1 N aqueous sodium hydroxide (30 mL) was stirred at room temperature for 18 hours. Mixture was concentrated to remove most of the ethanol. Resulting aqueous solution was acidified with acetic acid (2.5 g, 41.6 mmol). After standing for another 30 minutes, the precipitate formed was collected by filtration, washed with water and dried to give 3-methoxymethoxy-4-methyl-benzoic acid as a white powder. (Yield 3.82 g, 97%).

Workup

  1. concentrationMixture was concentrated
  2. customto remove most of the ethanol
  3. waitAfter standing for another 30 minutes
  4. customthe precipitate formed
  5. filtrationwas collected by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-17f00bad18d54b1a8060dc1e2b0d19e4
Source dataset
uspto-grants-2011_04
Patent number
US07932390B2

Reaction notes

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