Citric Acid → 3-Methoxy-2-naphthoic acid

HRID 491058

Reaktionsgleichung

Reaktionsgleichung von HRID 491058
[CH3:1][O:2][C:3]1[C:4]([C:13]([O:15]C)=[O:14])=[CH:5][C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2.O.[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO>[CH3:1][O:2][C:3]1[C:4]([C:13]([OH:15])=[O:14])=[CH:5][C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2

Komponenten

6

Edukt 4

HCID 311Citric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 296952Methyl 3-Methoxy-2-naphthoate

Produkt 1

HCID 701613-Methoxy-2-naphthoic acidAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of methyl 3-methoxy-2-naphthoate (6.28 g, 29.10 mmol) and water (10 mL) in MeOH (100 mL) at room temp. was treated with a 1 N NaOH solution (33.4 mL, 33.4 mmol). The mixture was heated at the reflux temp. for 3 h, cooled to room temp., and made acidic with a 10% citric acid solution. The resulting solution was extracted with EtOAc (2×100 mL). The combined organic layers were washed with a saturated NaCl solution, dried (MgSO4) and concentrated under reduced pressure. The residue was triturated with hexane then washed several times with hexane to give 3-methoxy-2-naphthoic acid as a white solid (5.40 g, 92%): 1H-NMR (DMSO-d6) δ 3.88 (s, 3H), 7.34-7.41 (m, 2H), 7.49-7.54 (m, 1H), 7.83 (d, J=8.09 Hz, 1H), 7.91 (d, J=8.09 Hz, 1H), 8.19 (s, 1H), 12.83 (brs, 1H).

Aufarbeitung

  1. temperatureThe mixture was heated at the reflux temp
  2. temperaturecooled to room temp.
  3. extractionThe resulting solution was extracted with EtOAc (2×100 mL)
  4. washThe combined organic layers were washed with a saturated NaCl solution
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was triturated with hexane
  8. washthen washed several times with hexane

Quellen und Nachweise

ORD-Eintrag
ord-55694919fbfa4e109130c9e51d2a8992
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07528255B2

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