p-Toluenesulfonic acid → HCID 21521437, compound

Participants

Reaction Conditions

Reaction Steps

A coupling component for the preferred dye of this invention was prepared as follows: A mixture of 30 parts of 1-naphthylamine and 43 parts of tetrahydrofurfuryl alcohol was heated to 80°C. Glacial acrylic acid (16.5 parts) was then added dropwise over a 10 minute period at 80°-85°C. When the addition was complete, the mixture was heated to 90°-95°C. and held at that temperature for 17 hours. The reaction mixture was cooled to 30°C. p-Toluenesulfonic acid (12.5 parts) and toluene (40 parts) were then added and the mixture heated to 85°-95°C. to remove the toluene-water azeotrope. The mixture was cooled to 25°C., washed first with 10% aqueous sodium bicarbonate in order to remove the acidic catalyst, and then with water. The mixture was then heated with steam, distillation of the toluene-water azeotrope commencing at 85°C. The temperature gradually increased during the distillation until at 115°C., almost no distillate was apparent. The mixture was cooled to 85°C. and the lower organic layer was separated to yield 60.5 parts (73% yield) of tetrahydrofurfuryl-3-(1-naphthylamino)propionate having a purity of 76% when analyzed by vapor phase chromatography.

Provenance & Evidence