Sodium Hydroxide → 3-(methoxymethyl)benzoic Acid

HRID 732009Notes

Reaction equation

HRID 732009 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:15])[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][O:13][CH3:14])[CH:7]=1>CO.O1CCCC1>[CH3:14][O:13][CH2:12][C:8]1[CH:7]=[C:6]([CH:11]=[CH:10][CH:9]=1)[C:5]([OH:15])=[O:4]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 23080888Methyl 3-(methoxymethyl)benzoate

Product 1

HCID 49623543-(methoxymethyl)benzoic AcidYield 99%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

1 N Sodium hydroxide (3.6 ml, 3.6 mmol) was added to a 3-methoxymethyl-benzoic acid methyl ester (436 mg, 2.4 mmol) in methanol (5 ml) and tetrahydrofuran (5 ml). The reaction was stirred at 70° C. for 30 min. and then the solvent was removed in vacuo. The residue was dissolved in a small amount of water and then acidified (pH about 2) by the addition of 1 N HCl (aq.). Following extraction of the aqueous layer with ethyl acetate, the organic layer was then washed with water and saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated to afford 395 mg (98%) of 3-methoxymethyl-benzoic acid as a white solid. 1H NMR (DMSO), δ (ppm): 7.90 (s, 1H), 7.87 (d, 1H), 7.56 (d, 1H), 7.48 (t, 1H), 4.48 (s, 2H), 3.31 (s, 3H).

Workup

  1. customthe solvent was removed in vacuo
  2. dissolutionThe residue was dissolved in a small amount of water
  3. additionby the addition of 1 N HCl (aq.)
  4. extractionextraction of the aqueous layer with ethyl acetate
  5. washthe organic layer was then washed with water and saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-aed5a73b9656424a852fe08f35684203
Source dataset
uspto-grants-2009_09
Patent number
US07585881B2

Reaction notes

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