Reaction #215519

Reaction equation

4-(2-cyclohexylethylamino)phenylacetic acid

lactic acid

toluenesulfonic acid

→

1-carboxyethyl 4-(2-cyclohexylethylamino)-phenylacetate

Solvents

toluene

Conditions

Workup

1. 1
   workup.ADDITIONA flask containing 10.0 g
2. 2
   workup.ADDITIONcharged
3. 3
   TemperatureThe solution is refluxed for 24 hours during which time the Soxhlet extractor
4. 4
   workup.ADDITIONis charged twice more with fresh sieves
5. 5
   FiltrationThe hot solution is filtered
6. 6
   workup.WAITleft
7. 7
   Temperatureto cool, whereupon 1-carboxyethyl 4-(2-cyclohexylethylamino)phenylacetate

Procedure

A flask containing 10.0 g. 4-(2-cyclohexylethylamino)phenylacetic acid, 3.3 g. lactic acid, 500 mg. toluenesulfonic acid and 500 ml. toluene equipped with a Soxhlet extractor charged with activated 4 A Linde molecular sieves. The solution is refluxed for 24 hours during which time the Soxhlet extractor is charged twice more with fresh sieves. The hot solution is filtered and left to cool, whereupon 1-carboxyethyl 4-(2-cyclohexylethylamino)phenylacetate separates as off-white crystals.

Source