2-Methoxybenzaldehyde → (2-Methoxyphenyl)(3-methyl-2-methoxymethoxyphenyl)methanol

HRID 2165011Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2165011
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH2:9][O:10][CH3:11].C([Li])CCC.[CH:17](=[O:26])[C:18]1[C:19]([O:24][CH3:25])=[CH:20][CH:21]=[CH:22][CH:23]=1.[Cl-].[NH4+]>CCCCCC.CN(C)CCN(C)C.O1CCCC1>[CH3:25][O:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[CH:17]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[C:3]=1[O:8][CH2:9][O:10][CH3:11])[OH:26]

Komponenten

8

Edukt 4

HCID 86582-MethoxybenzaldehydeHCID 25517Ammonium ChlorideHCID 38393511-(Methoxymethoxy)-2-methylbenzeneHCID 178418339Butyllithium

Produkt 1

HCID 19812676(2-Methoxyphenyl)(3-methyl-2-methoxymethoxyphenyl)methanolAusbeute 137,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 8028TetrahydrofuranLösungsmittelHCID 8037N,N,N',N'-TetramethylethylenediamineLösungsmittelHCID 8058HexaneLösungsmittel

Versuchsvorschrift

1-Methyl-2-methoxymethoxybenzene (15.2 g) was added to a mixture of 75 ml of a 1.6M solution of n-butyl lithium in hexane and 18.1 ml of tetramethylethylenediamine at 0° C. with stirring. After 4 hours, 13.6 g of o-anisaldehyde dissolved in 30 ml of tetrahydrofuran was added. The mixture was allowed to react for 0.5 hour and was then poured into a mixture of ice and saturated aqueous ammonium chloride. The resulting mixture was extracted with ether and the ether extract was dried over magnesium sulfate, filtered, and concentrated by evaporation under reduced pressure to obtain 39.5 g of the title compound as an off-white solid. The assigned structure was consistent with the proton NMR spectrum.

Aufarbeitung

  1. additionwas added
  2. customto react for 0.5 hour
  3. extractionThe resulting mixture was extracted with ether
  4. extractionthe ether extract
  5. dry with materialwas dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated by evaporation under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-36fb8446f5ba4263ad0bae982778668e
Quelldatensatz
uspto-grants-1990_07
Patentnummer
US04938790

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