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

HRID 260993

Reaktionsgleichung

Reaktionsgleichung von HRID 260993
[O:1]([C:8]1[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=1[CH:10]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(=[CH:35][C:36]([O:38]C)=[O:37])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.C(OCC)(=O)C>[O:1]([C:8]1[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=1[CH:10]=[CH:35][C:36]([OH:38])=[O:37])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 88060o-Phenoxybenzaldehyde

Produkt 1

HCID 7374222-Phenoxycinnamic acidAusbeute 54,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 2-phenoxybenzaldehyde (2.12 g; 10.70 mmol) and methyl (triphenylphos-phoranylidene)acetate (4.01 g; 11.76 mmol) in 60 mL of THF was refluxed overnight. The reaction was cooled, diluted with ethyl acetate (50 mL) and washed with water (3X). The crude residue Was purified on a silica gel column eluting with hexane to obtain 1.4 g (52%) of 2-phenoxycinnamic acid, 1H NMR (CDCl3): δ 3.78 (s, 3H); 6.56 (d, 1H, J=16.1); 6.87 (d, 1H, J=8.5); 7.00 (d, 2H, J=7.5); 7.10-7.15 (m,2H); 7.28-7.33 (m, 3H); 7.36 (d, 1H, J=8.5); 8.02 (d, 2H, J=16.2).

Aufarbeitung

  1. temperaturewas refluxed overnight
  2. temperatureThe reaction was cooled
  3. washwashed with water (3X)
  4. customThe crude residue Was purified on a silica gel column
  5. washeluting with hexane

Quellen und Nachweise

ORD-Eintrag
ord-a8900e45d32d489691ea99f6badda0e4
Quelldatensatz
uspto-grants-1996_06
Patentnummer
US05530157

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