反应详情

温度

5 °C

To a 1 L lab flask are added 54.6 g (0.26 mol, 99.9%) of 4-trifluoromethyl-2-nitroaniline, PETROSUL H-60 (5.3 g dissolved in 121.4 g water), 2-cumyl-4-tert-octylphenol (80.9 g, 0.25 mol, 92.5%) and ligroine (241.7 g, bp 90-110° C.). Sulfuric acid (32.7g, 93%) is charged to the reactor with stirring. The reaction mass is cooled to 5° C. Nitrosylsulfuric acid (94.4 g, 0.30 mol, 40% in sulfuric acid) and water (84.5 g) are added via a peristaltic pump over 8 hours. The cooling bath is removed and the reaction mass is allowed to warm to room temperature overnight. The reaction mass is heated to 40° C. Stirring is stopped and the two phases separate. Removed the aqueous layer. The ligroine layer weighed 373.8 g and contained 25.73 weight % of desired product (96.2 g of monoazo corresponding to a yield of 77% based on phenol as determined by calibrated HPLC analysis). The product may be crystallized from hot methanol, resulting in a burgundy solid with a melting point of 101-105° C. as per co-pending application 09/632217 example 10. 1H-NMR (CDCl3; 499.8494 MHz): δ 0.85 (s, 9H); δ 1.42 (s, 6H); δ 1.77 (s, 2H); δ 1.78 (s, 6H); δ 7.14-7.30 (multiplet, 5H); δ 7.50 (d, 1H); δ 7.90 (d, 1H); δ 8.15 (d, 1H); δ 8.37 (s, 1H).

1. additionTo a 1 L lab flask are added
2. customThe cooling bath is removed
3. temperatureto warm to room temperature overnight
4. temperatureThe reaction mass is heated to 40° C
5. stirringStirring
6. customthe two phases separate
7. customRemoved the aqueous layer
8. customThe product may be crystallized from hot methanol
9. customresulting in a burgundy solid with a melting point of 101-105° C. as per co-pending application 09/632217 example 10