Acetone → 4-Chloro-3,5-dimethylanisole

HRID 1070889

Reaktionsgleichung

Reaktionsgleichung von HRID 1070889
[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([OH:9])=[CH:4][C:3]=1[CH3:10].[CH3:11]C(C)=O.C(=O)([O-])[O-].[K+].[K+].IC>O>[CH3:11][O:9][C:5]1[CH:6]=[C:7]([CH3:8])[C:2]([Cl:1])=[C:3]([CH3:10])[CH:4]=1

Komponenten

6

Edukt 4

HCID 180AcetoneHCID 27234-Chloro-3,5-dimethylphenolHCID 6328Methyl iodideHCID 11430Potassium Carbonate

Produkt 1

HCID 5984974-Chloro-3,5-dimethylanisoleAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a 1 L round-bottom flask 4-chloro-3,5-dimethylphenol 63 (20 g, 127.7 mmol) and acetone (500 mL, 0.2 M) was placed. To this solution were added potassium carbonate (35.3 g, 255.4 mmol) and iodomethane (63.44 g, 447 mmol). The reaction was stirred and heated to reflux for 3 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The separated organic layer was washed with brine, dried over magnesium sulfate and concentrated. The crude product was purified by silica gel chromatography eluted with hexane to yield 4-chloro-3,5-dimethylphenyl methyl ether 64 (16.88 g, 77%). 1HNMR (300 MHz, CDCl3): δ 2.41 (s, 3H), 2.59 (s, 3H), 2.62 (s, 3H), 2.68 (s, 3H), 3.82 (s, 3H), 4.06 (s, 3H), 4.11 (s, 2H), 5.97 (d, 1H), 6.44 (s, 1H), 6.70 (s, 1H), 7.15 (d, 1H), 8.41 (brd, 1H), 10.31 (brd, 1H), APCI-MS m/z 468.2 (M+H)+.

Aufarbeitung

  1. temperatureheated
  2. temperatureto reflux for 3 hours
  3. extractionextracted with ethyl acetate
  4. washThe separated organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe crude product was purified by silica gel chromatography
  8. washeluted with hexane

Quellen und Nachweise

ORD-Eintrag
ord-4be58e7c21a04df98ea9e9504934580f
Quelldatensatz
uspto-grants-2005_06
Patentnummer
US06903132B2

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