Chloromethyl Methyl Ether → 2'-Hydroxy-4',6'-bis(methoxymethoxy)-3'-(3-methyl2-butenyl)acetophenone

HRID 2254193

Reaktionsgleichung

Reaktionsgleichung von HRID 2254193
[OH:1][C:2]1[C:7]([CH2:8][CH:9]=[C:10]([CH3:12])[CH3:11])=[C:6]([OH:13])[CH:5]=[C:4]([OH:14])[C:3]=1[C:15](=[O:17])[CH3:16].C(N(CC)C(C)C)(C)C.[CH3:27][O:28][CH2:29]Cl.[O:31]1[CH2:35]CC[CH2:32]1>>[OH:1][C:2]1[C:7]([CH2:8][CH:9]=[C:10]([CH3:12])[CH3:11])=[C:6]([O:13][CH2:27][O:28][CH3:29])[CH:5]=[C:4]([O:14][CH2:32][O:31][CH3:35])[C:3]=1[C:15](=[O:17])[CH3:16]

Komponenten

5

Edukt 4

HCID 7864Chloromethyl Methyl EtherHCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 11687311Ethanone, 1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-

Produkt 1

HCID 110993722'-Hydroxy-4',6'-bis(methoxymethoxy)-3'-(3-methyl2-butenyl)acetophenone

Versuchsvorschrift

Then, 30.0 g of 2',4',6'-trihydroxy-3'-(3-methyl- 2-butenyl)acetophenone was dissolved in tetrahydrofuran and 131.7 ml of N,N-diisopropylethylamine was added to the solution, and the mixture was stirred for 1 hour. Then, 48.0 ml of chloromethyl methyl ether was dropped into the mixture and the mixture was stirred for 3 hours. The mixture was extracted with dimethyl ether, and the organic layer was washed with water, dried with anhydrous sodium sulfate and concentrated under reduced pressure. Crystallization from ethyl acetate gave 21.5 g of 2'-hydroxy-4',6'-bis(methoxymethoxy)-3'-(3-methyl-2-butenyl)acetophenone.

Aufarbeitung

  1. stirringthe mixture was stirred for 3 hours
  2. extractionThe mixture was extracted with dimethyl ether
  3. washthe organic layer was washed with water
  4. dry with materialdried with anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customCrystallization from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-cecbc79ca79842c8ad87a23fede799d7
Quelldatensatz
uspto-grants-1993_08
Patentnummer
US05234951

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