Ethyl 4-formylbenzoate → HCID 53678243, Verbindung

HRID 485029

Reaktionsgleichung

Reaktionsgleichung von HRID 485029
[Br-].[CH3:2][C:3]1([CH3:35])[C:11]2[CH:10]=[C:9]([CH:12]([P+](C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH3:13])[S:8][C:7]=2[C:6]([CH3:34])([CH3:33])[CH2:5][CH2:4]1.[CH2:36]([O:38][C:39]([C:41]1[CH:48]=[CH:47][C:44]([CH:45]=O)=[CH:43][CH:42]=1)=[O:40])[CH3:37]>C1OCCC1>[CH3:35][C:3]1([CH3:2])[C:11]2[CH:10]=[C:9]([C:12]([CH3:13])=[CH:45][C:44]3[CH:47]=[CH:48][C:41]([C:39]([O:38][CH2:36][CH3:37])=[O:40])=[CH:42][CH:43]=3)[S:8][C:7]=2[C:6]([CH3:34])([CH3:33])[CH2:5][CH2:4]1

Komponenten

4

Edukt 2

HCID 80498Ethyl 4-formylbenzoateHCID 23049224[1-(4,5,6,7-Tetrahydro-4,4,7,7-tetramethylbenzo-[b]thien-2-yl)ethyl]triphenylphosphonium bromide

Produkt 1

HCID 53678243HCID 53678243, VerbindungAusbeute 55,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

30 g of [1-(4,5,6,7-tetrahydro-4,4,7,7-tetramethylbenzo[b]thien-2-yl)ethyl]triphenylphosphonium bromide and 9.5 g of 4-ethoxycarbonylbenzaldehyde are suspended in 300 ml of butylene oxide and the mixture is heated at reflux for 4 hours. The thus-obtained solution is concentrated to one third of the original volume in a water-jet vacuum, poured into 500 ml of a methanol/water mixture (6:4) and extracted several times with hexane. The organic phase is washed three times with water, dried over sodium sulphate and evaporated. There is obtained a light brownish oil which is purified by filtration over silica gel (eluting agent hexane/ether 19:1). After recrystallization from hexane, there are obtained 11.3 g of ethyl p-[2-(4,5,6,7-tetrahydro-4,4,7,7-tetramethylbenzo[b]thien-2-yl)propenyl]benzoate in the form of colorless crystals, m.p. 118°-120° C.

Aufarbeitung

  1. temperaturethe mixture is heated
  2. temperatureat reflux for 4 hours
  3. concentrationThe thus-obtained solution is concentrated to one third of the original volume in a water-jet vacuum
  4. additionpoured into 500 ml of a methanol/water mixture (6:4)
  5. extractionextracted several times with hexane
  6. washThe organic phase is washed three times with water
  7. dry with materialdried over sodium sulphate
  8. customevaporated
  9. customThere is obtained a light brownish oil which
  10. filtrationis purified by filtration over silica gel (eluting agent hexane/ether 19:1)
  11. customAfter recrystallization from hexane, there

Quellen und Nachweise

ORD-Eintrag
ord-ef232bc2c15c474b963e18a78783ada8
Quelldatensatz
uspto-grants-1985_08
Patentnummer
US04535086

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