Potassium Carbonate → 5-[[6-([1,1'-Biphenyl]-4-yloxy) hexyl]oxy]-2-hydroxybenzoic acid methyl ester

HRID 488322Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 488322
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:5]=1[OH:11].[C:13]1([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]Br)=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.CN(C=O)C>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([O:10][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][O:19][C:16]2[CH:15]=[CH:14][C:13]([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)=[CH:18][CH:17]=2)[CH:7]=[CH:6][C:5]=1[OH:11]

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 75077Methyl GentisateHCID 234323996-([1,1'-Biphenyl]-4-yloxy)hexyl bromide

Produkt 1

HCID 545134655-[[6-([1,1'-Biphenyl]-4-yloxy) hexyl]oxy]-2-hydroxybenzoic acid methyl esterAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 1.0 g (6 mmol) of 2,5-dihydroxybenzoic acid methyl ester, 2.0 g (6 mmol) of 6-([1,1'-biphenyl]-4-yloxy)hexyl bromide and 1.24 g (9 mmol) of potassium carbonate in 50 ml of acetone and 5 ml of DMF was stirred at reflux for 27 hours. The solvents were removed at reduced pressure, water was added to the residue and the product was extracted with ethyl acetate. The dried extract was concentrated to a solid which was purified by chromatography on 40 g of silica gel using 50% toluene-hexane to give 1.4 g (56% yield, mp 91°-92°) of 5-[[6-([1,1'-biphenyl]4-yloxy)hexyl]oxy]-2-hydroxybenzoic acid methyl ester. The structure was confirmed by nmr and mass spectra.

Aufarbeitung

  1. temperatureat reflux for 27 hours
  2. customThe solvents were removed at reduced pressure, water
  3. additionwas added to the residue
  4. extractionthe product was extracted with ethyl acetate
  5. extractionThe dried extract
  6. concentrationwas concentrated to a solid which
  7. customwas purified by chromatography on 40 g of silica gel using 50% toluene-hexane

Quellen und Nachweise

ORD-Eintrag
ord-a19262170b614899affda64e2eb4271a
Quelldatensatz
uspto-grants-1994_03
Patentnummer
US05298652

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