Réaction #1669078

Équation de réaction

diethyl azodicarboxylate

4,4′-dihydroxybiphenyl

8-chloro-1-octanol

triphenylphosphine

→

4′-[(8-chlorooctyl)oxy]-4-biphenylol

Rendement 40.0%

Solvants

tetrahydrofuran

tetrahydrofuran

water

Conditions de réaction

Traitement

1. 1
   Extractionextracted with ethyl acetate (3×150 ml)
2. 2
   LavageThe combined organic layers were washed with water (2×150 ml)
3. 3
   Séchagedried over magnesium sulphate
4. 4
   Filtrationfiltered
5. 5
   AutreThe solvent was removed in vacuo
6. 6
   AutreThe residue (19.2 g) was purified by flash chromatography on a silica gel column

Mode opératoire

A solution of diethyl azodicarboxylate (3.5 g; 20 mmol) and tetrahydrofuran (10 ml) was added dropwise at 0° C. to a solution of 4,4′-dihydroxybiphenyl (7.4 g; 40 mmol), 8-chloro-1-octanol (3.3 g; 20 mmol), triphenylphosphine (5.2 g; 20 mmol) and tetrahydrofuran (120 ml) and stirred at room temperature 72 h. The reaction mixture was added to water (400 ml) and extracted with ethyl acetate (3×150 ml). The combined organic layers were washed with water (2×150 ml), dried over magnesium sulphate and filtered. The solvent was removed in vacuo. The residue (19.2 g) was purified by flash chromatography on a silica gel column using a toluene/ethyl acetate mixture (95:5) as eluent, to give 2.6 g (40%) of 4′-[(8-chlorooctyl)oxy]-4-biphenylol.

Source