Reaktion #155823

Reaktionsgleichung

methyl p-hydroxybenzoate

1,5-pentanediol

triphenylphosphine

→

title compound

Ausbeute 68.0%

Methyl 4-[(5-hydroxypentyl)oxy]benzoate

Ausbeute 68.0%

Lösungsmittel

tetrahydrofuran

diethylazodicarboxylate

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenThe reaction mixture was concentrated
2. 2
   Waschenthe residue was washed with n-hexane-ethyl acetate solution (n-hexane:ethyl acetate=1:1)
3. 3
   EinengenThe reaction mixture was concentrated
4. 4
   Sonstigepurified by silica gel chromatography (n-hexane:ethyl acetate=64:36→45:55)

Vorschrift

To a solution of methyl p-hydroxybenzoate (3.38 g), 1,5-pentanediol (2.30 g) and triphenylphosphine (5.96 g) in tetrahydrofuran (100 mL), diethylazodicarboxylate (2.2N toluene solution, 10 mL) was slowly added under ice cooling. The reaction mixture was stirred under ice cooling for 16 hours. The reaction mixture was concentrated and the residue was washed with n-hexane-ethyl acetate solution (n-hexane:ethyl acetate=1:1). The reaction mixture was concentrated and then purified by silica gel chromatography (n-hexane:ethyl acetate=64:36→45:55) to obtain the title compound (3.58 g) having the following physical properties.

Quelle