Methyl iodide → 1-Chloro-4-hydroxy-4-methylnonane

HRID 258599

Reaktionsgleichung

Reaktionsgleichung von HRID 258599
I[CH3:2].[Mg].[Cl:4][CH2:5][CH2:6][CH2:7][C:8](=[O:14])[CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]>CCOCC>[Cl:4][CH2:5][CH2:6][CH2:7][C:8]([OH:14])([CH3:2])[CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 5462224MagnesiumHCID 203861031-Chlorononan-4-one

Produkt 1

HCID 203276741-Chloro-4-hydroxy-4-methylnonane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

The Grignard reagent prepared from iodomethane (14.2 g., 0.1 mole) and magnesium (2.4 g., 0.1 mole) in ether solution is added, dropwise to an ether solution of 1-chloro-4-nonanone (Example A, Step 1) (17.6 g., 0.1 mole). The reaction is refluxed gently for three hours then cooled and poured carefully into ice water (300 ml.). The ether layer is separated, washed with brine, and dried over sodium sulfate. Removal of the ether in vacuo gives 1-chloro-4-hydroxy-4-methylnonane as an oil. The tertiary alcohol is dissolved in pyridine and treated with one molar equivalent of acetic anhydride at 60°-80° for 8-16 hours to give 1-chloro-4-acetoxy-4-methylnonane as a colorless oil.

Aufarbeitung

  1. temperatureThe reaction is refluxed gently for three hours
  2. temperaturethen cooled
  3. customThe ether layer is separated
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. customRemoval of the ether in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-a5dab223aef145f7ac998714dbc33b97
Quelldatensatz
uspto-grants-1977_07
Patentnummer
US04033996

Verknüpfte Notizen

Wird geladen…