4-heptylaniline

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 32.9 g (0.17 M) of 4-heptylaniline was cooled to 0° C. or below, 85 g of 10% aqueous hydrochloric acid solution was added, and then a solution of 12.1 g of sodium nitrite in 70 ml of water was added. During the addition, the mixture was cooled so as not to exceed 0° C. After the addition, the mixture was allowed to react for 30 minutes, transferred into a dropping funnel and added dropwise into 300 ml of an 8% NaOH aqueous solution containing 16 g of phenol held at 5° C. or below. After the addition, the mixture was stirred for 1 hour, and then 10% hydrochloric acid aqueous solution was added thereto until a pH of 5-6 to precipitate the reaction product. The precipitate was separated by filtration, washed with water and dried overnight under reduced pressure. After the drying, the product was washed with 500 ml of petroleum ether and further dried under reduced pressure to obtain 34.7 g (0.12 M) of 4-hydroxy-4'-heptylazobenzene. The yield was 71%. During the addition the mixture was cooled so as not to exceed 0° C After the addition to react for 30 minutes transferred into a dropping funnel held at 5° C. or below After the addition until a pH of 5-6 to precipitate the reaction product The precipitate was separated by filtration washed with water dried overnight under reduced pressure After the drying, the product was washed with 500 ml of petroleum ether further dried under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 32.9 g (0.17M) of 4-heptylaniline was cooled below 0° C. and 85 g of 10% aqueous hydrochloric acid solution was added thereto. To the mixture was then added dropwise an aqueous solution of 12.1 g of sodium nitrite in 70 ml of water while cooling the mixture so as not to exceed 0° C. After the dropwise addition, the reaction was continued for 30 minutes. The reaction mixture was transferred into a dropping funnel and added dropwise therefrom into 300 ml of an 8%-NaOH aqueous solution containing 16 g of phenol while the temperature was kept below 5° C. After the dropwise addition, stirring was continued for 1 hour, and thereafter a 10% aqueous hydrochloric acid solution was added until the pH reached 5 to 6 thereby precipitating the reaction product. The precipitate was placed on a filter, washed with water and dried under reduced pressure overnight. The dried product was washed with 500 ml of petroleum ether and dried under reduced pressure to obtain 34.7 g (0.12M) of 4-hydroxy-4'-heptylazobenzene. The yield was 70%. while cooling the mixture so as not to exceed 0° C After the dropwise addition The reaction mixture was transferred into a dropping funnel added dropwise was kept below 5° C After the dropwise addition was continued for 1 hour thereby precipitating the reaction product washed with water dried under reduced pressure overnight The dried product was washed with 500 ml of petroleum ether dried under reduced pressure