Triphenylphosphine → 4-(2-(2,6-Dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)ethyl)benzaldehyde

HRID 2305059Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2305059
[OH:1][CH2:2][CH2:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1.[Cl:12][C:13]1[CH:18]=[C:17]([O:19][CH2:20][CH:21]=[C:22]([Cl:24])[Cl:23])[CH:16]=[C:15]([Cl:25])[C:14]=1O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[Cl:12][C:13]1[CH:18]=[C:17]([O:19][CH2:20][CH:21]=[C:22]([Cl:23])[Cl:24])[CH:16]=[C:15]([Cl:25])[C:14]=1[O:1][CH2:2][CH2:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 113467384-(3,3-Dichloro-2-propenyloxy)-2,6-dichlorophenolHCID 184247214-(2-Hydroxyethyl)benzaldehyde

Produkt 1

HCID 184295564-(2-(2,6-Dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)ethyl)benzaldehydeAusbeute 69 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a mixture of 3.88 g of 4-(2-hydroxyethyl)benzaldehyde, 6.7 g of 2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenol, 100 ml of tetrahydrofuran, and 6.0 g of triphenylphosphine was added dropwise a solution of 4.7 g of diisopropyl azodicarboxylate dissolved in 20 ml of tetrahydrofuran at the ice temperature over 1 hour. After completion of the addition, the reaction mixture was stirred at room temperature for 24 hours, and concentrated under reduced pressure. The residue was subjected to silica gel chromatography, which afforded 6.63 g (yield, 69%) of 4-(2-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)ethyl)benzaldehyde, m.p., 54. 2° C.

Aufarbeitung

  1. additionAfter completion of the addition
  2. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-12a841b0196640ac85d53bf17470969f
Quelldatensatz
uspto-grants-2002_08
Patentnummer
US06437184B1

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