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Sodium Hydroxide → 1,4-Diethoxynaphthalene-2,3-dicarboxylic acid

HRID 583908
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 583908
[CH2:1]([O:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([O:14][CH2:15][CH3:16])=[C:6]([C:17]([O-:19])=[O:18])[C:5]=1[C:20]([O:22]CC)=[O:21])[CH3:2].[OH-].[Na+]>C(O)C.O>[CH2:15]([O:14][C:7]1[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:4]([O:3][CH2:1][CH3:2])=[C:5]([C:20]([OH:22])=[O:21])[C:6]=1[C:17]([OH:19])=[O:18])[CH3:16]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 86592169Ethyl 1,4-diethoxy-2,3-naphthalenedicarboxylate

Produkt 1

HCID 223445251,4-Diethoxynaphthalene-2,3-dicarboxylic acidAusbeute 92,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Ethyl 1,4diethoxy-2,3-naphthalenedicarboxylate (32 g, 89 mmol) was added to a solution of sodium hydroxide (20 g) in ethanol (200 ml) and water (40 ml) and stirred for 1.5 h at 60° C. The reaction was cooled and the thick white suspension was filtered. The solid was dissolved in a mixture of ethyl acetate (200 ml) and water (800 ml). The layers were separated and the aqueous was acidified with hydrochloric acid (2M, 120 ml). The aqueous was extracted with ethyl acetate (2×) and the combined organics were dried (MgSO4). Evaporation of the solvent under vacuum gave the title compound as a white solid (25 g, 92%). δH [2H6]—DMSO 13.26,(2H, s), 8.15,(2H, m), 7.72,(2H, m), 4.13,(4H, q), 1.42,(6H, t).

Aufarbeitung

  1. temperatureThe reaction was cooled
  2. filtrationthe thick white suspension was filtered
  3. dissolutionThe solid was dissolved in a mixture of ethyl acetate (200 ml) and water (800 ml)
  4. customThe layers were separated
  5. extractionThe aqueous was extracted with ethyl acetate (2×)
  6. dry with materialthe combined organics were dried (MgSO4)
  7. customEvaporation of the solvent under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-d43cc72eea124f52ac241f129d75e50b
Quelldatensatz
uspto-grants-2005_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06924297B2

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