Reaktion #575504

Reaktionsgleichung

2,5-dihydroxybenzoic acid methyl ester

6-([1,1'-biphenyl]-4-yloxy)hexyl bromide

potassium carbonate

→

5-[[6-([1,1'-biphenyl]4-yloxy)hexyl]oxy]-2-hydroxybenzoic acid methyl ester

Ausbeute 56.0%

Lösungsmittel

acetone

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturat reflux for 27 hours
2. 2
   SonstigeThe solvents were removed at reduced pressure, water
3. 3
   workup.ADDITIONwas added to the residue
4. 4
   Extraktionthe product was extracted with ethyl acetate
5. 5
   ExtraktionThe dried extract
6. 6
   Einengenwas concentrated to a solid which
7. 7
   Sonstigewas purified by chromatography on 40 g of silica gel using 50% toluene-hexane

Vorschrift

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.

Quelle