Chloromethyl Methyl Ether → 2-Methoxy-1-phenylethanone

HRID 1030688

Reaktionsgleichung

Reaktionsgleichung von HRID 1030688
O[C:2]1[CH:7]=[C:6](O)[CH:5]=[C:4](O)[C:3]=1[C:10](=[O:12])[CH3:11].C(N(CC)C(C)C)(C)C.[CH3:22][O:23]CCl>O1CCCC1>[CH3:22][O:23][CH2:11][C:10]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:2]=1)=[O:12]

Komponenten

5

Edukt 3

HCID 7864Chloromethyl Methyl EtherHCID 680732',4',6'-TrihydroxyacetophenoneHCID 81531Diisopropylethylamine

Produkt 1

HCID 776982-Methoxy-1-phenylethanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

In 200 ml of anhydrous tetrahydrofuran were dissolved 30 g of 2',4',6'-trihydroxyacetophenone and 115.0 g of N,N-diisopropylethylamine, and 50.2 g of chloromethyl methyl ether was gradually added to the solution under ice cooling over a period of 20 minutes and the reaction mixture was stirred under ice cooling for 1 hour and at room temperature for 4 hours to effect reaction. After the reaction, the reaction mixture was extracted with 3 l of ether, and the ether layer was washed with water (500 ml×3 times), shaken with a saturated aqueous solution of sodium chloride (300 ml×2 times), dried with anhydrous sodium sulfate, and filtered. The solvent was removed from the filtrate by distillation and the obtained residue was recrystallized from a mixed solvent of methanol and water to obtain 18.9 g (yield=41.4%) of 2'-hydroxy-4',6'-bis(methoxyacetophenone in the form of a colorless prism.

Aufarbeitung

  1. additionwas gradually added to the solution under ice cooling over a period of 20 minutes
  2. customreaction
  3. customAfter the reaction
  4. extractionthe reaction mixture was extracted with 3 l of ether
  5. washthe ether layer was washed with water (500 ml×3 times)
  6. stirringshaken with a saturated aqueous solution of sodium chloride (300 ml×2 times)
  7. dry with materialdried with anhydrous sodium sulfate
  8. filtrationfiltered
  9. customThe solvent was removed from the filtrate by distillation
  10. customthe obtained residue was recrystallized from a mixed solvent of methanol and water

Quellen und Nachweise

ORD-Eintrag
ord-67ac17e98d9249d1acf9eb381098a0d1
Quelldatensatz
uspto-grants-1992_04
Patentnummer
US05106871

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