Methyl 3-bromo-1-adamantaneacetate → Methyl 3-phenyl-1-adamantaneacetate

HRID 21682

Reaktionsgleichung

Reaktionsgleichung von HRID 21682
[C:1]1([C:7]23[CH2:16][CH:11]4[CH2:12][CH:13]([CH2:15][C:9]([CH2:17][C:18]([OH:20])=[O:19])([CH2:10]4)[CH2:8]2)[CH2:14]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:22]12CC3CC(CC(CC(OC)=O)(C3)C1)C2.[Cl-].[Cl-].[Cl-].[Al+3]>C1C=CC=CC=1>[C:1]1([C:7]23[CH2:16][CH:11]4[CH2:12][CH:13]([CH2:15][C:9]([CH2:17][C:18]([O:20][CH3:22])=[O:19])([CH2:10]4)[CH2:8]2)[CH2:14]3)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

5

Edukt 3

HCID 610084Methyl 3-bromo-1-adamantaneacetateHCID 2771107(3-Phenyl-1-adamantyl)acetic acidHCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 53665692Methyl 3-phenyl-1-adamantaneacetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

Preparation of 3-Phenyl-l-adamantaneacetic acid, a hapten. Methyl 3-bromoadamantaneacetate (80 g) (Aldrich Chemical Co. Milwaukee Wis.) was dissolved in benzene (1.6 L) under nitrogen. Aluminum trichloride (37.12 g) was added portionwise over 75 min. at ambient temperature. The reaction mixture was then quenched by the addition of 0.5M phosphoric acid (1.6 L). The layers were separated and the organic layer was dried over sodium sulfate, filtered, and evaporated in vacuo to give methyl 3-phenyl-1-adamantaneacetate (80 g).

Aufarbeitung

  1. customThe reaction mixture was then quenched by the addition of 0.5M phosphoric acid (1.6 L)
  2. customThe layers were separated
  3. dry with materialthe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-4e36a21ee6d845b586893d9fe90a7e86
Quelldatensatz
uspto-grants-1995_06
Patentnummer
US05424414

Verknüpfte Notizen

Wird geladen…