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2,3-Dihydroxybutanedioic Acid → 4-[(5,6,7,8-Tetrahydro-5,5,8,8-tetramethylnaphth-2-yl)ethynyl]-benzaldehyde

HRID 1657142
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1657142
[H-].C([Al+]CC(C)C)C(C)C.[CH3:11][C:12]1([CH3:34])[CH2:21][CH2:20][C:19]([CH3:23])([CH3:22])[C:18]2[CH:17]=[C:16]([C:24]#[C:25][C:26]3[CH:33]=[CH:32][C:29]([C:30]#N)=[CH:28][CH:27]=3)[CH:15]=[CH:14][C:13]1=2.C(O)(=O)C(C(C(O)=O)O)[OH:37]>CCCCCC.CCOCC>[CH3:11][C:12]1([CH3:34])[CH2:21][CH2:20][C:19]([CH3:23])([CH3:22])[C:18]2[CH:17]=[C:16]([C:24]#[C:25][C:26]3[CH:33]=[CH:32][C:29]([CH:30]=[O:37])=[CH:28][CH:27]=3)[CH:15]=[CH:14][C:13]1=2
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Komponenten

6

Edukt 3

HCID 8752,3-Dihydroxybutanedioic AcidHCID 136048264-[(5,6,7,8-Tetrahydro-5,5,8,8-tetramethylnaphth-2-yl)ethynyl]-benzonitrileHCID 21225700Diisobutylaluminumhydride

Produkt 1

HCID 197869634-[(5,6,7,8-Tetrahydro-5,5,8,8-tetramethylnaphth-2-yl)ethynyl]-benzaldehydeAusbeute 38 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283
Diethyl Ether
Lösungsmittel
HCID 8058HexaneLösungsmittel

Versuchsvorschrift

56 ml (67 millimoles) of a 20% strength solution of diisobutylaluminum hydride in hexane were added to a solution of 10 g (32 millimoles) of 4-[(5,6,7,8-tetrahydro- 5,5,8,8-tetramethylnaphth-2-yl)-ethynyl]-benzonitrile (Example 1) in 120 ml of absolute ether. The mixture was stirred for a further 40 minutes, 150 ml of saturated tartaric acid solution were added dropwise and stirring was continued for a further hour. Thereafter, the mixture was extracted three times with ether and the combined ether phases were washed twice with water, dried over Na2SO4 and evaporated down. Recrystallization of the residue from isopropanol gave 3.8 g (38%) of the title compound of melting point 130° C.

Aufarbeitung

  1. stirringstirring
  2. waitwas continued for a further hour
  3. extractionThereafter, the mixture was extracted three times with ether
  4. washthe combined ether phases were washed twice with water
  5. dry with materialdried over Na2SO4
  6. customevaporated down
  7. customRecrystallization of the residue from isopropanol

Quellen und Nachweise

ORD-Eintrag
ord-c4b16abd25bd451ebd72047157bfd36b
Quelldatensatz
uspto-grants-1993_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05256694

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