Potassium Carbonate → Methyl 6-(4-acetyl-3-hydroxy-2-propylphenoxy)hexanoate

HRID 1249008

Reaktionsgleichung

Reaktionsgleichung von HRID 1249008
[OH:1][C:2]1[C:7]([CH2:8][CH2:9][CH3:10])=[C:6]([OH:11])[CH:5]=[CH:4][C:3]=1[C:12](=[O:14])[CH3:13].Br[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([O:23][CH3:24])=[O:22].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:24][O:23][C:21](=[O:22])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][O:11][C:6]1[CH:5]=[CH:4][C:3]([C:12](=[O:14])[CH3:13])=[C:2]([OH:1])[C:7]=1[CH2:8][CH2:9][CH3:10]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 27751982',4'-Dihydroxy-3'-propylacetophenoneHCID 4170292Methyl 6-Bromohexanoate

Produkt 1

HCID 14330007Methyl 6-(4-acetyl-3-hydroxy-2-propylphenoxy)hexanoateAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 2.72 g of 1-(2,4-dihydroxy-3-propylphenyl)ethanone, 2.72 g of methyl 6-bromohexanoate and 2.90 g of anhydrous potassium carbonate in 30 ml of anhydrous dimethyl formamide was stirred and heated at 75° for 7 hours. The usual workup followed by chromatography on 200 g of silica gel and elution with 10% ethyl acetate-toluene gave 2.77 g (62% yield) of 6-(4-Acetyl-3-hydroxy-2-propylphenoxy)hexanoic acid methyl ester, the titled compound, as an oil.

Aufarbeitung

  1. temperatureheated at 75° for 7 hours
  2. washThe usual workup followed by chromatography on 200 g of silica gel and elution with 10% ethyl acetate-toluene

Quellen und Nachweise

ORD-Eintrag
ord-7682505a954f4e2b847c1446a4761817
Quelldatensatz
uspto-grants-1986_12
Patentnummer
US04628115

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