StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

1,2-Epoxybutane → 9-(2,6-Dichloro-4-methoxy-5-methyl-phenyl)-3,7-dimethyl-nona-2,4,6,8-tetraen-1-oic acid ethyl ester

HRID 2286787
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2286787
[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]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 5

HCID 78341,2-EpoxybutaneHCID 11776TriphenylphosphineHCID 234625772,6-Dichloro-4-methoxy-3-methyl-benzyl chlorideHCID 54295620Ethyl 3,7-dimethyl-8-oxoocta-2,4,6-trienoateHCID 86736665(2,6-Dichloro-3-methyl-4-methoxybenzyl) triphenyl phosphonium chloride

Produkt 1

HCID 127591
9-(2,6-Dichloro-4-methoxy-5-methyl-phenyl)-3,7-dimethyl-nona-2,4,6,8-tetraen-1-oic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21889329Toluene hexaneLösungsmittel

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

  1. additionAfter the addition of 120 ml
  2. extractionexhaustively extracted with methanol/water (60:40 parts by volume)
  3. customThe resulting solution is evaporated under reduced pressure
  4. customThe oily residue is purified by adsorption on silica gel
  5. washfor the elution

Quellen und Nachweise

ORD-Eintrag
ord-e3a9f53bc67c459d91366ca557797bf1
Quelldatensatz
uspto-grants-1981_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04267382

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion