1,2-Dichloroethane → 3,3,4,4,4-Pentafluorobutan-2-yl 4-formylbenzoate

HRID 1181641Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1181641
[C:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1)([OH:3])=[O:2].[F:12][C:13]([F:21])([C:17]([F:20])([F:19])[F:18])[CH:14](O)[CH3:15].C(Cl)CCl.CCCCCC>CN(C1C=CN=CC=1)C.CN(C=O)C>[CH:8]([C:7]1[CH:10]=[CH:11][C:4]([C:1]([O:3][CH:14]([C:13]([F:21])([F:12])[C:17]([F:20])([F:19])[F:18])[CH3:15])=[O:2])=[CH:5][CH:6]=1)=[O:9]

Komponenten

7

Edukt 4

HCID 111,2-DichloroethaneHCID 8058HexaneHCID 120884-Formylbenzoic acidHCID 789913,3,4,4,4-Pentafluorobutan-2-ol

Produkt 1

HCID 589307223,3,4,4,4-Pentafluorobutan-2-yl 4-formylbenzoateAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 4-carboxybenzaldehyde (21.9 g, 145.9 mmol), 3,3,4,4,4-pentafluoro-2-butanol (24.1 g, 146.9 mmol), EDC (33.5 g, 174.8 mmol) and DMAP (18.1 g, 148.1 mmol) was dissolved in DMF (60 ml) at rt. It was stirred for 36 h at rt. Hexane was added, it was washed with 1 N HCl, sat NaHCO3 and brine. The aqueous layers were extracted three times with hexane. It was dried over Na2SO4, filtered, concentrated, and the residue was purified by silica gel chromatography (ethyl acetate:hexane 1:10) to yield the desired aldehyde as a yellow oil (67%).

Aufarbeitung

  1. washit was washed with 1 N HCl
  2. extractionThe aqueous layers were extracted three times with hexane
  3. dry with materialIt was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customthe residue was purified by silica gel chromatography (ethyl acetate:hexane 1:10)

Quellen und Nachweise

ORD-Eintrag
ord-1e5678f6c80c457082468b9d3fa8fb52
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07285671B2

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