Reaction #56595

Reaction equation

1-[4-(4-(dimethylamino)naphthylazo)phenylazo]-4-hydroxy-naphtalene

6-iodohexyl acrylate

potassium carbonate

→

1-[4-(4-(dimethylamino)naphthylazo)-phenylazo]-4-(6-acryloyloxyhexyloxy)naphtalene

Yield 84.4%

Solvents

DMF

Conditions

Workup

1. 1
   TemperatureAfter cooling to room temperature the reaction mixture
2. 2
   Otherwas quenched with 100 ml 3N HCl
3. 3
   Filtrationthe resulting precipitate was filtered off
4. 4
   Washwashed with water (100 ml) and ethanol (50 ml)

Procedure

A mixture consisting of 0.44 g of 1-[4-(4-(dimethylamino)naphthylazo)phenylazo]-4-hydroxy-naphtalene, 0.56 g of 6-iodohexyl acrylate, and 0.28 g of potassium carbonate in 10 ml of DMF was stirred under nitrogen atmosphere for 3 h at 60° C. After cooling to room temperature the reaction mixture was quenched with 100 ml 3N HCl and the resulting precipitate was filtered off, washed with water (100 ml) and ethanol (50 ml) to give 0.5 g of pure 1-[4-(4-(dimethylamino)naphthylazo)-phenylazo]-4-(6-acryloyloxyhexyloxy)naphtalene as a brownish powder; λmax. (CB 483): 504 nm.

Source