Reaction #527338

Reaction equation

amyl nitrite

4-anisidine

2-ethylhexyl acrylate

sulfuric acid

2-ethylhexanol

→

2-ethylhexyl p-methoxycinnamate

Solvents

water

Conditions

Workup

1. 1
   workup.ADDITIONafter addition
2. 2
   Temperatureis heated in the course of 1 hour to 65° C.
3. 3
   workup.STIRRINGstirred for 12 hours at this temperature
4. 4
   Extractionextracted with 200 ml of dichloromethane

Procedure

12.3 g of 4-anisidine (4-methoxyaniline) are mixed with stirring with 10 ml of concentrated sulfuric acid and 60 ml of 2-ethylhexanol and the mixture is cooled to about 10° C. 11.7 g of amyl nitrite are then slowly added and the mixture is stirred for a further 40 minutes after addition is completed. 20.2 g of 2-ethylhexyl acrylate and 100 mg of Pd (5% by weight of Pd on activated charcoal) are then added to the reaction mixture which is heated in the course of 1 hour to 65° C. and stirred for 12 hours at this temperature. The mixture is diluted with 100 ml of water and extracted with 200 ml of dichloromethane. As studies by thin-layer chromatography and gas chromatography show, 2-ethylhexyl p-methoxycinnamate has not formed even in the smallest amounts. The 2-ethylhexyl acrylate used is present essentially in unchanged form.

Source