Triphenylphosphine → (6-Carboxyhexyl)triphenylphosphonium bromide

HRID 1283188

Reaktionsgleichung

Reaktionsgleichung von HRID 1283188
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]([OH:10])=[O:9].[C:11]1([P:17]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(#N)C>[Br-:1].[C:8]([CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][P+:17]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)([OH:10])=[O:9]

Komponenten

4

Edukt 2

HCID 11776TriphenylphosphineHCID 1217237-Bromoheptanoic acid

Produkt 1

HCID 11027094(6-Carboxyhexyl)triphenylphosphonium bromide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of 63.6 g. of 7-bromoheptanoic acid 80 g. of triphenylphosphine, and 300 ml. of acetonitrile is refluxed for 68 hours. Then 200 ml. of acetonitrile is removed by distillation. After the remaining solution has cooled to room temperature, 300 ml. of benzene is added with stirring. After forming a crystal, the mixture is allowed to stand overnight. The solid which separates is collected by filtration giving 134.1 g. of the product as white prisms, melting point 185°-187° C. A portion is recrystallized from methanol-ether affording white prisms, melting point 185°-187°. The infrared spectrum shows absorptions at 2850, 2570, 2480, 1710, 1585, 1485, 1235, 1200, 1185, 1160, 1115, 1000, 755, 725, and 695 cm.-1NMR peaks are observed at 1.2-1.9, 2.1-2.6, 3.3-4.0, and 7.7-8.0 δ.

Aufarbeitung

  1. additionA mixture of 63.6 g
  2. customof acetonitrile is removed by distillation
  3. additionof benzene is added
  4. customAfter forming a crystal
  5. filtrationThe solid which separates is collected by filtration
  6. customgiving 134.1 g
  7. customA portion is recrystallized from methanol-ether affording white prisms, melting point 185°-187°

Quellen und Nachweise

ORD-Eintrag
ord-b8900420f844424cab3546fe01a7b423
Quelldatensatz
uspto-grants-1976_08
Patentnummer
US03974195

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