Triphenylphosphine → Phosphonium, (6-carboxyhexyl)triphenyl-, bromide

HRID 262807

Reaktionsgleichung

Reaktionsgleichung von HRID 262807
[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 11027094Phosphonium, (6-carboxyhexyl)triphenyl-, bromide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of 63.6 g. of 7-bromoheptanoic acid in 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 adding a seed crystal, the mixture is allowed to stand overnight. The solid which separated is collected by filtration giving 134.1 g. of the product as white prisms, melting point 185°-187°. 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. additionAfter adding a seed crystal
  5. customThe solid which separated
  6. filtrationis collected by filtration
  7. customgiving 134.1 g
  8. customA portion is recrystallized from methanol-ether affording white prisms, melting point 185°-187°

Quellen und Nachweise

ORD-Eintrag
ord-29d0759d2f364f3a861ab51221b2f31d
Quelldatensatz
uspto-grants-1979_05
Patentnummer
US04154950

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