Nonanoic Acid → 4-Nonanoyloxy-2,3,5,6-tetrafluorophenol

HRID 1587256

Reaktionsgleichung

Reaktionsgleichung von HRID 1587256
[F:1][C:2]1[C:8]([F:9])=[C:7]([OH:10])[C:6]([F:11])=[C:5]([F:12])[C:3]=1[OH:4].[C:13](O)(=[O:22])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21].C1(N=C=NC2CCCCC2)CCCCC1.N1(C2C=CN=CC=2)CCCC1>O1CCCC1>[C:13]([O:4][C:3]1[C:2]([F:1])=[C:8]([F:9])[C:7]([OH:10])=[C:6]([F:11])[C:5]=1[F:12])(=[O:22])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Komponenten

6

Edukt 4

HCID 8158Nonanoic AcidHCID 10868DicyclohexylcarbodiimideHCID 698702,3,5,6-TetrafluorohydroquinoneHCID 755674-Pyrrolidinopyridine

Produkt 1

HCID 98368414-Nonanoyloxy-2,3,5,6-tetrafluorophenolAusbeute 32,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

2.0 g (11.0 mM) of 2,3,5,6-tetrafluorohydroquinone, 0.87 g (5.5 mM) of nonanoic acid, 1.13 g (5.5 mM) of dicyclohexylcarbodiimide and a catalytic amount of 4-pyrrolidinopyridine were added to 20 ml of tetrahydrofuran, followed by stirring for 3 hours at room temperature. After the reaction, the insoluble residue was filtered off, followed by distilling-off of the solvent to obtain a crude product. The crude product was purified by silica gel column chromatography (eluent: toluene) to obtain 0.57 g of an objective product (Yield: 32.2%).

Aufarbeitung

  1. customAfter the reaction
  2. filtrationthe insoluble residue was filtered off
  3. customto obtain a crude product
  4. customThe crude product was purified by silica gel column chromatography (eluent: toluene)

Quellen und Nachweise

ORD-Eintrag
ord-8c25d2d156a546659dde293fdae77464
Quelldatensatz
uspto-grants-1993_06
Patentnummer
US05217643

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