Nitric Acid → 5-Nitro-2,3-dihydro-1H-indene-2-carboxylic acid

HRID 1267158Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1267158
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[C:10]([OH:12])=[O:11].S(=O)(=O)(O)O.[N+:18]([O-])([OH:20])=[O:19]>CCOCC>[N+:18]([C:6]1[CH:5]=[C:4]2[C:9](=[CH:8][CH:7]=1)[CH2:1][CH:2]([C:10]([OH:12])=[O:11])[CH2:3]2)([O-:20])=[O:19]

Komponenten

5

Edukt 3

HCID 944Nitric AcidHCID 1118Sulfuric Acid2×HCID 5757772-Indancarboxylic Acid

Produkt 1

HCID 185458885-Nitro-2,3-dihydro-1H-indene-2-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

A solution of indane-2-carboxylic Acid 9a (18.8 g) in ether (250 ml) was added to conc. sulfuric acid (300 ml) (temp.=3-13° C.). To this mixture, a solution of conc. nitric acid (4.4 ml) and conc. sulfuric acid (100 ml) was added (temp.=−1° C.). The mixture was stirred at 2-8° C. for 1 h, poured onto ice, and the aqueous phase was extracted with ether. The combined organic extracts were washed with brine, dried (MgSO4) and evaporated to dryness in vacuo. The residue was crystallized from ether to give 5-nitroindane-2-carboxylic acid (6.0 g). The solid was dissolved in CH2Cl2 (100 ml) and DMF (1 ml). Thionyl chloride (8.4 ml) was added, and the solution was boiled under reflux for 5 hours. Evaporation in vacuo gave the title compound (8.6 g).

Aufarbeitung

  1. additionpoured onto ice
  2. extractionthe aqueous phase was extracted with ether
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated to dryness in vacuo
  6. customThe residue was crystallized from ether

Quellen und Nachweise

ORD-Eintrag
ord-5caeca0af494482ca8f6e6fa04276a81
Quelldatensatz
uspto-grants-2003_04
Patentnummer
US06552044B2

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