Citric Acid → 3-Methoxy-2-naphthoic acid

HRID 78295

Reaktionsgleichung

Reaktionsgleichung von HRID 78295
[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 (br s, 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-fe264895cfed464c85fe3abc39694b8a
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841330B2

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