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

HRID 2254205

Reaktionsgleichung

Reaktionsgleichung von HRID 2254205
[OH:1][C:2]1[C:7]([CH2:8][CH:9]=[C:10]([CH3:12])[CH3:11])=[C:6]([O:13][CH2:14][O:15][CH3:16])[CH:5]=[C:4]([O:17][CH2:18][O:19][CH3:20])[C:3]=1[C:21](=[O:23])[CH3:22].[H][H]>C(O)C>[OH:1][C:2]1[C:7]([CH2:8][CH2:9][CH:10]([CH3:12])[CH3:11])=[C:6]([O:13][CH2:14][O:15][CH3:16])[CH:5]=[C:4]([O:17][CH2:18][O:19][CH3:20])[C:3]=1[C:21](=[O:23])[CH3:22]

Komponenten

4

Edukt 2

HCID 110993722'-Hydroxy-4',6'-bis(methoxymethoxy)-3'-(3-methyl2-butenyl)acetophenoneHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 160945312'-Hydroxy-3'-isopentyl-4',6'-bis(methoxymethoxy)acetophenoneAusbeute 82,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of 2.08 g of the 2'-hydroxy-4',6'-bis(methoxymethoxy)-3'-(3-methyl-2-butenyl)acetophenone obtained in Production Example 13 in ethanol (20 ml) was added to a sufficiently hydrogen gas-absorbed suspension of 1.0 g of 5% palladium-carbon in 30 ml of ethanol, and the mixture was stirred at room temperature under atmospheric pressure in a hydrogen atmosphere. After the reaction, the reaction mixture was filtered, and the solvent was removed from the filtrate by distillation. The obtained residue was subjected to the silica gel column chromatography (3.0 cm in diameter, 60 g of silica gel, 0.3 kg/cm2) using a mixed solvent of n-hexane and ethyl acetate (n-hexane/ethyl acetate-3/1). Fractions of 50 ml were recovered, and 1.73 g (yield=82.8%) of 2'-hydroxy-3'-isopentyl-4',6'-bis(methoxymethoxy)acetophenone in the form of a yellow oil was obtained from the third to fifth fractions.

Aufarbeitung

  1. customgas-absorbed
  2. additionsuspension of 1.0 g of 5% palladium-carbon in 30 ml of ethanol
  3. customAfter the reaction
  4. filtrationthe reaction mixture was filtered
  5. customthe solvent was removed from the filtrate by distillation
  6. customFractions of 50 ml were recovered

Quellen und Nachweise

ORD-Eintrag
ord-647ea5649e784bf594788f2ea2fee9e0
Quelldatensatz
uspto-grants-1993_08
Patentnummer
US05234951

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