Sodium Hydroxide → 3-(methoxymethyl)benzoic Acid

HRID 732009Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 732009
[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]

Komponenten

5

Edukt 2

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

Produkt 1

HCID 49623543-(methoxymethyl)benzoic AcidAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-aed5a73b9656424a852fe08f35684203
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07585881B2

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