Triphenylphosphine → (5-Carboxypentyl)triphenylphosphanium bromide

HRID 1657909Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1657909
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8].[C:10]1([P:16]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(#N)C>[Br-:1].[C:7]([CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][P+:16]([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)([OH:9])=[O:8]

Komponenten

4

Edukt 2

HCID 11776TriphenylphosphineHCID 202106-Bromohexanoic acid

Produkt 1

HCID 2779280(5-Carboxypentyl)triphenylphosphanium bromide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of 6-bromohexanoic acid (50 g.), triphenylphosphine (67.1 g.) and 240 ml. of acetonitrile is heated at reflux for 22 hr. Then 160 ml. of acetonitrile is removed by distillation. The solution is cooled and to it is added 240 ml. of benzene. The title compound is obtained as crystals, m.p. 201°-203° C.; infrared spectral absorptions at 2800, 1705, 1585, 1480, 1435, 1375, 1225, 1210, 1190, 1115, 745, 725, and 695 cm.-1 ; and NMR peaks at 1.5-1.9, 2.2-2.6, 3.3-4.0 and 7.7-8.0 (multiplet) δ.

Aufarbeitung

  1. temperatureat reflux for 22 hr
  2. customof acetonitrile is removed by distillation
  3. temperatureThe solution is cooled and to it
  4. additionis added 240 ml

Quellen und Nachweise

ORD-Eintrag
ord-e4a59badb837466ebda5c1a8b7840c9e
Quelldatensatz
uspto-grants-1976_06
Patentnummer
US03962293

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