Reaction #56594

Reaction equation

4-hydroxy-3-methyl4′-phenylazo-azobenzene

triphenylphosphine

diethyl azodicarboxylate

4-hydroxybutylacrylate

→

4-(4-Acryloyloxybutyloxy)-3-methyl-4′-phenylazo-azobenzene

Solvents

THF

THF

Conditions

Workup

1. 1
   workup.ADDITIONAfter complete addition
2. 2
   Concentrationconcentrated to dryness
3. 3
   FiltrationThe obtained yellow-red residue was purified by filtration on silica
4. 4
   Otherto give 0.65 g of pure yellow-orange crystalys

Procedure

To a solution of 0.63 g of 4-hydroxy-3-methyl4′-phenylazo-azobenzene, 1.05 g of triphenylphosphine and 0.58 g of 4-hydroxybutylacrylate in 10 ml THF; which was cooled to −30° C., was added dropwise a solution of 0.70 g of diethyl azodicarboxylate in 5 ml THF. After complete addition, the reaction mixture was stirred for further 45 min at room temperature, and then concentrated to dryness. The obtained yellow-red residue was purified by filtration on silica using methylenechloride as the eluent to give 0.65 g of pure yellow-orange crystalys; λmax. (CB 483): 395 nm.

Source