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Sulfuric Acid → HCID 23149682, Verbindung

HRID 555676
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 555676
[C:1]12([C:12]([O:14][CH3:15])=[O:13])[CH2:8][CH2:7][C:4]([C:9]([OH:11])=[O:10])([CH2:5][CH2:6]1)[CH2:3][CH2:2]2.S(=O)(=O)(O)O>ClCCl>[C:4]12([C:9]([O:11][C:1]([CH3:8])([CH3:6])[CH3:2])=[O:10])[CH2:3][CH2:2][C:1]([C:12]([O:14][CH3:15])=[O:13])([CH2:6][CH2:5]1)[CH2:8][CH2:7]2
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 1118Sulfuric AcidHCID 110420624-(Methoxycarbonyl)bicyclo[2.2.2]octane-1-carboxylic acid

Produkt 1

HCID 23149682HCID 23149682, VerbindungAusbeute 157,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Methyl hydrogen bicyclo[2.2.2]octane-1,4-dicarboxylate (500 mg) was dissolved in dichloromethane (5 mL) and sulfuric acid (50 μL) was added to the solution. The mixture was bubbled with isobutene for 5 minutes while chilled in a salt/ice bath. The mixture was then stirred for 4 hours at room temperature and was left for 4 days. Subsequently, the reaction mixture was diluted with dichloromethane (5 mL), washed sequentially with a saturated aqueous solution of sodium bicarbonate and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was dried under reduced pressure to give 1,1-dimethylethyl methyl bicyclo[2.2.2]octane-1,4-dicarboxylate (497 mg).

Aufarbeitung

  1. customThe mixture was bubbled with isobutene for 5 minutes
  2. temperaturewhile chilled in a salt/ice bath
  3. waitwas left for 4 days
  4. additionSubsequently, the reaction mixture was diluted with dichloromethane (5 mL)
  5. washwashed sequentially with a saturated aqueous solution of sodium bicarbonate and saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was dried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-8b5f4acfc1e84fd582f0b6042e60787a
Quelldatensatz
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08053465B2

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