Reaktionsgleichung
[Cl-].[Cl:2][C:3]1[CH:28]=[C:27]([O:29][CH3:30])[C:26]([CH3:31])=[C:25]([Cl:32])[C:4]=1[CH2:5][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.ClC1C(C)=C(OC)C=C(Cl)C=1CCl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:65]([O:67][C:68](=[O:79])[CH:69]=[C:70]([CH3:78])[CH:71]=[CH:72][CH:73]=[C:74]([CH:76]=O)[CH3:75])[CH3:66].C1OC1CC>C1(C)C=CC=CC=1.CCCCCC>[CH2:65]([O:67][C:68](=[O:79])[CH:69]=[C:70]([CH3:78])[CH:71]=[CH:72][CH:73]=[C:74]([CH3:76])[CH:75]=[CH:5][C:4]1[C:25]([Cl:32])=[C:26]([CH3:31])[C:27]([O:29][CH3:30])=[CH:28][C:3]=1[Cl:2])[CH3:66]Komponenten
Edukt 5
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
100 g. of 2,6-dichloro-4-methoxy-5-methyl-benzyl-triphenylphosphonium chloride, prepared from 52 g. of 2,6-dichloro-4-methoxy-3-methyl-benzyl chloride and 57 g. of triphenylphosphine, are treated with 42 g. of 7-formyl-3-methyl-octa-2,4,6-trien-1-oic acid ethyl ester. After the addition of 120 ml. of 1,2-butylene oxide, the resulting mixture is heated to 80°-85° C. for 4 hours while stirring. The mixture is diluted with toluene/hexane (1:1 parts by volume) and exhaustively extracted with methanol/water (60:40 parts by volume). The resulting solution is evaporated under reduced pressure. The oily residue is purified by adsorption on silica gel using toluene for the elution. 9-(2,6-dichloro-4-methoxy-5-methyl-phenyl)-3,7-dimethyl-nona-2,4,6,8-tetraen-1-oic acid ethyl ester is obtained from the eluate and melts at 100°-101° C. after recrystallization from benzene/hexane (50:50 parts by volume).
Aufarbeitung
- additionAfter the addition of 120 ml
- extractionexhaustively extracted with methanol/water (60:40 parts by volume)
- customThe resulting solution is evaporated under reduced pressure
- customThe oily residue is purified by adsorption on silica gel
- washfor the elution
Quellen und Nachweise
- ORD-Eintrag
- ord-c89e883b75a84e41afb4b1f8004b6ddf
- Quelldatensatz
- uspto-grants-1980_09
- Patentnummer
- US04225527
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