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4-(4-Nitro-3-benzyloxyphenoxy)-4'-(4-benzyloxycarbonylphenoxy)octafluorobiphenyl → 4-(4-Amino-3-hydroxyphenoxy)4'-(4-carboxyphenoxy)octafluorobiphenyl

HRID 2304996
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2304996
[N+:1]([C:4]1[CH:47]=[CH:46][C:7]([O:8][C:9]2[C:14]([F:15])=[C:13]([F:16])[C:12]([C:17]3[C:22]([F:23])=[C:21]([F:24])[C:20]([O:25][C:26]4[CH:31]=[CH:30][C:29]([C:32]([O:34]CC5C=CC=CC=5)=[O:33])=[CH:28][CH:27]=4)=[C:19]([F:42])[C:18]=3[F:43])=[C:11]([F:44])[C:10]=2[F:45])=[CH:6][C:5]=1[O:48]CC1C=CC=CC=1)([O-])=O.[H][H]>O1CCCC1.C(OCC)(=O)C.[Pd]>[NH2:1][C:4]1[CH:47]=[CH:46][C:7]([O:8][C:9]2[C:10]([F:45])=[C:11]([F:44])[C:12]([C:17]3[C:22]([F:23])=[C:21]([F:24])[C:20]([O:25][C:26]4[CH:27]=[CH:28][C:29]([C:32]([OH:34])=[O:33])=[CH:30][CH:31]=4)=[C:19]([F:42])[C:18]=3[F:43])=[C:13]([F:16])[C:14]=2[F:15])=[CH:6][C:5]=1[OH:48]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 2

HCID 118146894-(4-Nitro-3-benzyloxyphenoxy)-4'-(4-benzyloxycarbonylphenoxy)octafluorobiphenylHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 110499734-(4-Amino-3-hydroxyphenoxy)4'-(4-carboxyphenoxy)octafluorobiphenylAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysator
HCID 8028
Tetrahydrofuran
Lösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

49.9 g of the 4-(4-nitro-3-benzyloxyphenoxy)-4′-(4-benzyloxycarbonylphenoxy)octafluorobiphenyl prepared as described in Example 2 (0.065 mol) are dissolved in 400 ml of a mixture of tetrahydrofuran and ethyl acetate (volume ratio 1:1), and 5 g of Pd/C (palladium/carbon) are then added to the solution. The mixture is then hydrogenated using hydrogen at a pressure of 1 bar at room temperature in an autoclave with vigorous stirring; the reaction is terminated after 3 days. The yellow-beige solution is evaporated to half in a rotary evaporator and left to stand overnight at room temperature, during which the reaction product precipitates out in crystalline form. The reaction product is then separated off and dried for 48 hours under nitrogen at 40° C./10 mbar in a vacuum drying cabinet (yield: 91%).

Aufarbeitung

  1. additionare then added to the solution
  2. customat room temperature
  3. customthe reaction is terminated after 3 days
  4. customThe yellow-beige solution is evaporated to half in a rotary evaporator
  5. waitleft
  6. customthe reaction product precipitates out in crystalline form
  7. customThe reaction product is then separated off
  8. customdried for 48 hours under nitrogen at 40° C./10 mbar in a vacuum
  9. customdrying cabinet (yield: 91%)

Quellen und Nachweise

ORD-Eintrag
ord-8843cac3a15a4e05bbfb2495e4bc4067
Quelldatensatz
uspto-grants-2002_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06437178B2

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