反応 #1256708

反応方程式

hydrochloric acid

N2

NaOH

4

4-(4-methoxy-2,6-dimethyl-phenyl)-3,5-dimethyl-pyridine

→

4-(3,5-dimethyl-pyridin-4-yl)-3,5-dimethyl-phenol

溶媒

water

water

water

pyridine

反応条件

後処理

1. 1
   workup.DISTILLATIONwas distilled from the mixture until the temperature
2. 2
   その他rose to 210° C
3. 3
   その他the reaction flask was fitted with a reflux condenser
4. 4
   温度refluxed for 3 h at 210° C
5. 5
   その他The resulting reaction mixture
6. 6
   ろ過The resulting colorless precipitate was then collected by filtration
7. 7
   洗浄washed with water
8. 8
   その他to give 0.208 g (91.6%) of analytically pure product as a colorless solid

実験手順

To stirring pyridine (3 mL) was slowly added concentrated hydrochloric acid (3.3 mL). The reaction flask was then fitted for distillation, and water was distilled from the mixture until the temperature rose to 210° C. After cooling to 140° C., 4 (0.241 g, 1.00 mmol) was added to the above mixture, and the reaction flask was fitted with a reflux condenser connected to a N2 source. The yellow mixture was stirred and refluxed for 3 h at 210° C. The resulting reaction mixture was then diluted with warm water (3 mL) and slowly poured into hot water (20 mL). The resulting yellow solution was cooled to room temperature and neutralized with dilute NaOH solution to pH ˜7. The resulting colorless precipitate was then collected by filtration and washed with water to give 0.208 g (91.6%) of analytically pure product as a colorless solid: mp>270° C. (decomp.); 1H NMR (500 MHz, DMSO-d6): δ 9.245 (s, 1H), 8.337 (s, 2H), 6.579 (s, 2H), 1.841 (s, 6H), 1.729 (s, 6H); 13C NMR (125 MHz, DMSO-d6): δ 156.400, 148.191, 147.630, 134.949, 131.015, 127.197, 114.493, 19.359, 16.098; MS (ESI): m/z 228.4 [(M+H)+, 100]; Anal. Calcd. For C15H17NO: C, 79.26; H, 7.54; N, 6.16. Found: C, 79.14; H, 7.58; N, 6.18.

出典