Triphenylphosphine → Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester

HRID 1731564

Reaktionsgleichung

Reaktionsgleichung von HRID 1731564
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.BrCC(OC)=O.[Br-].[CH3:27][O:28][C:29]([CH2:31][P+:32]([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:30].[PH4+].[OH-].[Na+]>C1C=CC=CC=1.O>[CH3:27][O:28][C:29]([CH:31]=[P:32]([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)([C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)=[O:30]

Komponenten

8

Edukt 5

HCID 11776TriphenylphosphineHCID 14798Sodium HydroxideHCID 60984Methyl bromoacetateHCID 2733211Phosphonium, (2-methoxy-2-oxoethyl)triphenyl-, bromide (1:1)HCID 5460504Phosphonium

Produkt 1

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 241BenzeneLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

Triphenyl phosphine (13 g.) was dissolved in dry benzene (60 ml.) and methyl bromoacetate (8.3 g.) was added dropwise. The solution was heated at 70° C., for 2 days, and then cooled and filtered. The residue was washed with benzene and dried to give about 16 g. of (methoxycarbonyl methyl)triphenylphosphonium bromide. The phosphonium salt (10 g.) was dissolved in water (250 ml.) and 5% aqueous sodium hydroxide was added dropwise with stirring until the solution became alkaline to litmus. The resulting precipitate was filtered off, washed with water and dried. Crystallisation from ethyl acetate/petroleum spirit gave (methoxycarbonyl methylene) triphenyl phosphorane as a colourless solid in about 80% yield.

Aufarbeitung

  1. temperaturecooled
  2. filtrationfiltered
  3. washThe residue was washed with benzene
  4. customdried
  5. customto give about 16 g
  6. filtrationThe resulting precipitate was filtered off
  7. washwashed with water
  8. customdried
  9. customCrystallisation from ethyl acetate/petroleum spirit

Quellen und Nachweise

ORD-Eintrag
ord-3476553ebdfe4c05b6d48784eacaf486
Quelldatensatz
uspto-grants-1986_11
Patentnummer
US04622337

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