Chloromethyl Methyl Ether → 4-(Methoxymethoxy)-3-(3-methylbut-2-en-1-yl)benzaldehyde

HRID 1030697

Reaktionsgleichung

Reaktionsgleichung von HRID 1030697
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[CH2:10][CH:11]=[C:12]([CH3:14])[CH3:13].C(N(CC)C(C)C)(C)C.[CH3:24][O:25][CH2:26]Cl>O1CCCC1>[CH3:24][O:25][CH2:26][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[CH2:10][CH:11]=[C:12]([CH3:14])[CH3:13]

Komponenten

5

Edukt 3

HCID 7864Chloromethyl Methyl EtherHCID 81531DiisopropylethylamineHCID 4438533-Dimethylallyl-4-hydroxybenzaldehyde

Produkt 1

HCID 145597524-(Methoxymethoxy)-3-(3-methylbut-2-en-1-yl)benzaldehydeAusbeute 91,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Then, 7.0 g of the so-obtained 4-hydroxy-3-(3-methyl-2-butenyl)benzaldehyde was dissolved in770 ml of tetrahydrofuran, and 19.25 g of N,N-diisopropylethylamine was added to the solution and the mixture was stirred at room temperature for 1 hour. After the reaction, the reaction liquid was cooled to 0° C. and 7.0 ml of chloromethyl methyl ether was dropped into the reaction liquid, and the mixture was stirred at room temperature overnight. Then, the reaction liquid was poured into ice water, and the organic layer was extracted with ether, washed with water, dried with anhydrous sodium sulfate, and filtered. The obtained residue was subjected to the column chromatography (260 g of 200-400 mesh Kieselgel 60, hexane/ethyl acetate=6/1, 0.4 kg/cm2), fractions of 50 ml were recovered in sequence, and the 14th to 24th fractions were combined to obtain 7.85 g (yield=91.1%) of 4-methoxymethoxy-3-(3-methyl-2-butenyl)benzaldehyde in the form of a colorless liquid.

Aufarbeitung

  1. additionwas added to the solution
  2. customAfter the reaction
  3. customthe reaction liquid
  4. temperaturewas cooled to 0° C.
  5. stirringthe mixture was stirred at room temperature overnight
  6. customThen, the reaction liquid
  7. extractionthe organic layer was extracted with ether
  8. washwashed with water
  9. dry with materialdried with anhydrous sodium sulfate
  10. filtrationfiltered
  11. customwere recovered in sequence

Quellen und Nachweise

ORD-Eintrag
ord-7f5c29e1bbca4a719adc09e18bae46f2
Quelldatensatz
uspto-grants-1992_04
Patentnummer
US05106871

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