반응 #575504

반응 방정식

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

수율 56.0%

용매

acetone

DMF

반응 조건

후처리

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

실험 절차

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.

출처