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3-Chloro-2-methyl-1-propene → 2,5,5-Trimethylocta-1,6,7-trien-4-ol

HRID 483241
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 483241
[CH3:1][C:2](=[CH2:5])[CH2:3]Cl.[CH3:6][C:7]([CH3:13])([CH:10]=[C:11]=[CH2:12])[CH:8]=[O:9].[NH4+].[Cl-]>CCOCC>[CH3:1][C:2]([CH2:3][CH:8]([OH:9])[C:7]([CH3:13])([CH3:6])[CH:10]=[C:11]=[CH2:12])=[CH2:5]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 112413-Chloro-2-methyl-1-propeneHCID 25517Ammonium ChlorideHCID 776782,2-Dimethyl-3,4-pentadienal

Produkt 1

HCID 36994162,5,5-Trimethylocta-1,6,7-trien-4-olAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Reaktionsbedingungen

Temperatur
15 °C

Versuchsvorschrift

300 ml of absolute ether were added to 7.29 g (0.30 mole) of dry Mg, the mixture was cooled to 15±1° C., and 27.19 g (0.30 mole) freshly distilled β-methylallyl chloride were added. The mixture was stirred over night at the same temperature. The white suspension was cooled to 0° C., and 11.03 g (0.10 mole) 1a in 150 ml absolute ether were added dropwise during 1 hour. The mixture was stirred at 0° C. for 4 hours (reaction monitored on GC). 37 ml of saturated NH4Cl solution were added with vigorous stirring. The solution was decanted from the magnesium salts which were washed several times with ether. The combined ether phases were dried (MgSO4). Distillation gave 14.22 g (91%) 2a, b.p. 60°-1° C./1.5 mm Hg.

Aufarbeitung

  1. temperatureThe white suspension was cooled to 0° C.
  2. stirringThe mixture was stirred at 0° C. for 4 hours
  3. custom(reaction monitored on GC)
  4. customThe solution was decanted from the magnesium salts which
  5. washwere washed several times with ether
  6. dry with materialThe combined ether phases were dried (MgSO4)
  7. distillationDistillation

Quellen und Nachweise

ORD-Eintrag
ord-f7c6d9ae663c4a18aefa7d835ca2caef
Quelldatensatz
uspto-grants-1986_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04578484

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