Methyl iodide → 4-(Methoxymethyl)benzonitrile

HRID 2407072

Reaktionsgleichung

Reaktionsgleichung von HRID 2407072
[OH:1][CH2:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1.[H-].[Na+].CI.[C:15](OCC)(=O)C.CCCCCC>C1COCC1.O>[CH3:15][O:1][CH2:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1

Komponenten

7

Edukt 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 160549p-Cyanobenzyl alcoholHCID 21226206Ethyl acetate hexane

Produkt 1

HCID 132851414-(Methoxymethyl)benzonitrileAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

4-(Hydroxymethyl)benzonitrile (6.0 g, 45.09 mmol) was dissolved in THF (60 mL), cooled to −5° C. to −10° C. and treated with sodium hydride (2.16 g, 90.19 mmol). The resulting mixture was stirred for 30 minutes then treated with methyl iodide (9.6 g, 67.65 mmol) at RT for 2 hours. After completion of the reaction (TLC; ethyl acetate/Hexane, 5:5), the mixture was poured into water (50 mL) and extracted with ethyl acetate (3×25 mL). The separated organic layers were combined, dried over Na2SO4 and concentrated in vacuo. The crude compound was purified by gradient flash chromatography, eluting with 5% ethyl acetate in hexane to afford 4-(methoxymethyl)benzonitrile (6.7 g, 90%).

Aufarbeitung

  1. temperaturecooled to −5° C. to −10° C.
  2. extractionextracted with ethyl acetate (3×25 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe crude compound was purified by gradient flash chromatography
  6. washeluting with 5% ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-c8956d390fcb4f44bc595e4161a51489
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08809525B2

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