Реакция #575504

Уравнение реакции

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

Выход 56.0%

Растворители

acetone

DMF

Условия реакции

Обработка

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

Методика

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.

Источник