Sodium Hydroxide → 5-(Benzyloxy)-4-methoxy-2-nitrobenzoic acid

HRID 61641Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 61641
[CH2:1]([O:8][C:9]1[C:10]([O:28][CH3:29])=[CH:11][C:12]([N+:25]([O-:27])=[O:26])=[C:13]([CH:24]=1)[C:14]([O:16]CC1C=CC=CC=1)=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>CCO.O>[CH2:1]([O:8][C:9]1[C:10]([O:28][CH3:29])=[CH:11][C:12]([N+:25]([O-:27])=[O:26])=[C:13]([CH:24]=1)[C:14]([OH:16])=[O:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 2

HCID 14798Sodium Hydroxide2×HCID 59362000Benzyl 5-(benzyloxy)-4-methoxy-2-nitrobenzoate

Produkt 1

HCID 8212205-(Benzyloxy)-4-methoxy-2-nitrobenzoic acidAusbeute 94,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of benzyl 5-(benzyloxy)-4-methoxy-2-nitrobenzoate (1.4 g, 3.56 mmol) in EtOH (10 mL) was added 1N NaOH (4.27 mL, 4.27 mmol). The mixture was stirred at RT for 1 h, upon which an additional aliquot of NaOH (4.27 mL, 4.27 mmol) was added. Stirring was continued at RT overnight. The mixture was diluted with water (20 mL) and washed with CH2Cl2 (2×25 mL). The aqueous layer was acidified to pH=2 with 0.5 N HCl and extracted with EtOAc (3×50 mL). The combined organics were dried (Na2SO4), filtered and concentrated in vacuo to give 5-(benzyloxy)-4-methoxy-2-nitrobenzoic acid (1.02 g, 3.37 mmol, 94%).

Aufarbeitung

  1. additionwas added
  2. washwashed with CH2Cl2 (2×25 mL)
  3. extractionextracted with EtOAc (3×50 mL)
  4. dry with materialThe combined organics were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-007ec04edc194beba37d00a8bb54a777
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09440961B2

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