Epichlorohydrin → 2-[[4-(2-Fluoroethoxy)phenoxy]methyl]oxirane

HRID 1774310

Reaktionsgleichung

Reaktionsgleichung von HRID 1774310
[OH-].[Na+].[F:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1.[CH2:14]([CH:16]1[O:18][CH2:17]1)Cl.CCOC(C)=O>O>[F:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH:16]2[CH2:17][O:18]2)=[CH:9][CH:8]=1

Komponenten

6

Edukt 4

HCID 7835EpichlorohydrinHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 150586584-(2-Fluoroethoxy)phenol

Produkt 1

HCID 867130932-[[4-(2-Fluoroethoxy)phenoxy]methyl]oxiraneAusbeute 48 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A solution of NaOH (0.35 g) in 10 mL of water was added to a mixture of 4-(2-f luoroethoxy) phenol (1.10 g, 7.1 mmol) and epichlorohydrin (0.80 mL, 10.2 mmol). The mixture was heated at 100° C. for 3 h. After cooling, the mixture is taken up with AcOEt (50 mL). The organic phase was separated, washed with brine, dried over Na2SO4 and evaporated under reduced pressure. The crude residue was chromatographed (Petroleum ether/AcOEt, 4:1, as eluent) to afford pure compound in 48% yield. 1H NMR (CDCl3): δ 2.60-2.70 (m, 2H), 3.16 (m, 1H), 3.89-4.04 (m, 2H), 4.17-4.28 (m, 1H), 4.50-4.65 (m, 1H), 6.54 -6.60 (m, 2H), 6.84-6.87 (m, 2H).

Aufarbeitung

  1. temperatureAfter cooling
  2. customThe organic phase was separated
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. customevaporated under reduced pressure
  6. customThe crude residue was chromatographed (Petroleum ether/AcOEt, 4:1, as eluent)
  7. customto afford pure compound in 48% yield

Quellen und Nachweise

ORD-Eintrag
ord-c8ad2e8ee1c1450c8a3355303c420a31
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09260400B2

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