Water → HCID 54099954, Verbindung

HRID 894153Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 894153
[OH-].[Na+].[CH3:3][O:4][C@H:5]1[CH2:10][CH2:9][CH2:8][CH2:7][C@H:6]1[OH:11].[F:12][C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1[CH2:15]Cl.O>CS(C)=O>[F:12][C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1[CH2:15][O:11][C@@H:6]1[CH2:7][CH2:8][CH2:9][CH2:10][C@@H:5]1[O:4][CH3:3]

Komponenten

6

Edukt 4

HCID 962WaterHCID 9580Benzene, 1-(chloromethyl)-2-fluoro-HCID 14798Sodium HydroxideHCID 6951180(1R,2S)-2-methoxycyclohexanol

Produkt 1

HCID 54099954HCID 54099954, VerbindungAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

772 g (19.3 mol) of sodium hydroxide powder were added in portions to 1,672 g (12.8 mol) of cis-2-methoxycyclohexanol and 1,853 g (12.8 mol) of 2-fluorobenzyl chloride in 10 l of dimethylsulphoxide, whilst cooling with water. The mixture was stirred at 35° C. for 2 hours and at 45° C. overnight. Thereafter, it was cooled to 18° C., 10 l of petroleum ether were added and the mixture was discharged onto 10 ml of ice-water. The organic phase was separated off, extracted by shaking with water, dried over sodium sulphate and filtered and the filtrate was concentrated. The oily residue was distilled. 2,685 g (87.5% of theory) of cis-1-(2-fluorobenzyloxy)-2-methoxy-cyclohexane of boiling point 150° C./2 mm Hg were obtained.

Aufarbeitung

  1. temperatureThereafter, it was cooled to 18° C.
  2. customThe organic phase was separated off
  3. extractionextracted
  4. stirringby shaking with water
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated
  8. distillationThe oily residue was distilled

Quellen und Nachweise

ORD-Eintrag
ord-9d8e949cac07436c8befbd2faccf123f
Quelldatensatz
uspto-grants-1981_08
Patentnummer
US04282388

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