Sodium Hydroxide → 1-(Ethyloxy)-4-[(phenylmethyl)oxy]-2,3-naphthalenedicarboxylic acid

HRID 222431Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 222431
[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][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:6]([C:22]([O:24]CC)=[O:23])[C:5]=1[C:27]([O:29]CC)=[O:28])[CH3:2].[OH-].[Na+]>C(O)C>[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][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[C:6]([C:22]([OH:24])=[O:23])[C:5]=1[C:27]([OH:29])=[O:28])[CH3:2]

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 58012512Diethyl 1-(ethyloxy)-4-[(phenylmethyl)oxy]-2,3-naphthalenedicarboxylate

Produkt 1

HCID 580124801-(Ethyloxy)-4-[(phenylmethyl)oxy]-2,3-naphthalenedicarboxylic acidAusbeute 96,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of diethyl 1-(ethyloxy)-4-[(phenylmethyl)oxy]-2,3-naphthalenedicarboxylate (3.05 g, 7.23 mmol), ethanol (30 ml), and 2N aqueous sodium hydroxide solution (35 ml) was refluxed for 3 hours. The reaction mixture was cooled and evaporated. This was acidified with HCl (2N) and extracted with ethyl acetate twice. Combined organics were dried over magnesium sulphate and the solvent evaporated to give the title compound as a white solid (2.55 g, 6.97 mmol). LC/MS: Rt=2.76, [MH]− 365.

Aufarbeitung

  1. temperaturewas refluxed for 3 hours
  2. temperatureThe reaction mixture was cooled
  3. customevaporated
  4. extractionextracted with ethyl acetate twice
  5. dry with materialCombined organics were dried over magnesium sulphate
  6. customthe solvent evaporated

Quellen und Nachweise

ORD-Eintrag
ord-d162371733ad4c0cb011c193a73568c8
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08207213B2

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