Carbon Dioxide → 1H-indene-3-carboxylic acid

HRID 654447Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 654447
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.CCCC.[C:14](=[O:16])=[O:15].Cl>C(OCC)C.O>[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:14]([OH:16])=[O:15])=[CH:2]1

Komponenten

7

Edukt 4

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 7219IndeneHCID 7843Butane

Produkt 1

HCID 842611H-indene-3-carboxylic acidAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

To a stirred solution of indene (21.9 mL, 188 mmol) in 150 mL of dry ethyl ether was added 129 mL (200 mmol) of η-BuLi dropwise at room temperature over 30 minutes with the evolution of butane. The rust colored mixture was refluxed for 2 h, and then poured in a thin stream onto 40 g of Dry Ice. The mixture was shaken at room temperature for 2 h, after which time 1 L of H2O was cautiously added. The aqueous layer was acidified with 10% HCl and then extracted with ethyl ether. Recrystallization from benzene gave 20 g (80%) of indene-3-carboxylic acid as yellowish crystals.

Aufarbeitung

  1. extractionextracted with ethyl ether
  2. customRecrystallization from benzene

Quellen und Nachweise

ORD-Eintrag
ord-6124f256bb3b44ddba6b14da7e0dcdb8
Quelldatensatz
uspto-grants-1992_07
Patentnummer
US05132313

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