Boron trifluoride etherate → p-Aminophenylacetic acid ethyl ester

A solution of 8.2 g. of p-aminophenylacetic acid, 150 ml. of absolute ethanol, and 3 ml. of boron trifluoride etherate is heated to reflux for 15 hrs. The solution is concentrated to ca. 50 ml. by distillation of the solvent and then evaporated to dryness in vacuo. The residue is dissolved in ethyl ether, washed with aqueous sodium bicarbonate, dried and evaporated to yield ethyl p-aminophenylacetate. A mixture of 5.0 g. of this amine, 9.4 g. of 1-bromohexadecane, 4.2 g. of anhydrous potassium carbonate and 40 ml. of hexamethylphosphoramide is heated to 80° C. for 7 hours. The mixture is then cooled, diluted with water and extracted with ethyl ether. The ether extracts are washed with water, dried and evaporated. The residue is recrystallized from a mixture of chloroform and hexane, yielding ethyl (4-hexadecylaminophenyl)acetate.

1. temperatureto reflux for 15 hrs
2. concentrationThe solution is concentrated to ca. 50 ml
3. distillationby distillation of the solvent
4. customevaporated to dryness in vacuo
5. dissolutionThe residue is dissolved in ethyl ether
6. washwashed with aqueous sodium bicarbonate
7. customdried
8. customevaporated

ORD record

ord-98fb4596a93040a58e9961033ef0b275

Source dataset

uspto-grants-1982_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04348399