Naphthalene → 4-(1-Naphthyl)-4-oxobutanoic acid

HRID 1290678

Reaktionsgleichung

Reaktionsgleichung von HRID 1290678
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[C:11]1(=[O:17])[O:16][C:14](=[O:15])[CH2:13][CH2:12]1.[Cl-].[Cl-].[Cl-].[Al+3]>[N+](C1C=CC=CC=1)([O-])=O>[C:9]1([C:11]([CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[O:17])[C:10]2[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=2)[CH:6]=[CH:7][CH:8]=1

Komponenten

5

Edukt 3

HCID 931NaphthaleneHCID 7922Succinic anhydrideHCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 2777864-(1-Naphthyl)-4-oxobutanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7416NitrobenzeneLösungsmittel

Versuchsvorschrift

A mixture of naphthalene (40 g) and succinic anhydride (20 g) was added to a well stirred suspension of aluminum trichloride (55 g) in nitrobenzene (140 ml). The resulting mixture was stirred overnight at room temperature. The mixture was then poured slowly onto ice-water (600 g) and acidified with 6N-hydrochloric add. The crude acid was filtered, washed with water until washings were neutral and recrystallized from ethanol yielding the product (m.p. 170°-172° C.).

Aufarbeitung

  1. additionwas added to a well
  2. stirringThe resulting mixture was stirred overnight at room temperature
  3. additionThe mixture was then poured slowly onto ice-water (600 g)
  4. filtrationThe crude acid was filtered
  5. washwashed with water until washings
  6. customrecrystallized from ethanol yielding the product (m.p. 170°-172° C.)

Quellen und Nachweise

ORD-Eintrag
ord-024b5ec1d33346db85bbe6514f8530a5
Quelldatensatz
uspto-grants-1998_05
Patentnummer
US05753642

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