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Sulfuric Acid → 4-tert.butyl 1-(4nitrobenzyl) 2(R)-isobutylsuccinate

HRID 982566
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 982566
[CH2:1]([C@H:5]([CH2:19][C:20]([OH:22])=[O:21])[C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=1)=[O:7])[CH:2]([CH3:4])[CH3:3].[CH2:23]=[C:24]([CH3:26])[CH3:25].S(=O)(=O)(O)O.C(=O)([O-])O.[Na+]>C(OCC)C.O>[CH2:1]([C@H:5]([CH2:19][C:20]([O:22][C:24]([CH3:26])([CH3:25])[CH3:23])=[O:21])[C:6]([O:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([N+:16]([O-:18])=[O:17])=[CH:14][CH:15]=1)=[O:7])[CH:2]([CH3:4])[CH3:3]
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Komponenten

7

Edukt 4

HCID 1118Sulfuric AcidHCID 8255IsobutyleneHCID 516892Sodium BicarbonateHCID 541390571-(4-nitrobenzyl) hydrogen 2(R)-isobutylsuccinate

Produkt 1

HCID 585602894-tert.butyl 1-(4nitrobenzyl) 2(R)-isobutylsuccinateAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962
Water
Lösungsmittel
HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

9.4 g of 1-(4-nitrobenzyl) hydrogen 2(R)-isobutylsuccinate were dissolved in 30 ml of dry diethyl ether and the solution was cooled in a dry-ice/acetone bath. There were then added 70 ml of isobutene, followed dropwise by 0.64 ml of concentrated sulfuric acid. The reaction flask was tightly topped and the mixture was stirred at room temperature for 2 days. The mixture was made basic with saturated sodium hydrogen carbonate solution and water was added. The organic phase was separated and the aqueous phase was extracted twice more with diethyl ether. The combined ethereal phases were washed with water and saturated sodium chloride solution, dried over anhydrous sodium sulfate and evaporated to give 8.8 g (77%) of 4-tert.butyl 1-(4nitrobenzyl) 2(R)-isobutylsuccinate in the form of an oil. Rf (System A) 0.87.

Aufarbeitung

  1. temperaturethe solution was cooled in a dry-ice/acetone bath
  2. additionwas added
  3. customThe organic phase was separated
  4. extractionthe aqueous phase was extracted twice more with diethyl ether
  5. washThe combined ethereal phases were washed with water and saturated sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-6729c9e341df48cdbdffa3a3b1bce6ea
Quelldatensatz
uspto-grants-1991_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04996358

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