反应详情

温度

20 °C

To a freshly prepared solution of 2-iodo-4-(1,1-dimethylethyl)phenol (5.5 g., 0.02 mole) in a mixture of acetic acid (27 ml.) and sulfuric acid (3 ml.) is added powdered 2-chloro-N-(hydroxymethyl)acetamide (2.5 g., 0.02 mole) with stirring at 20° C. over a 10 minute period. After 2.5 hours the orange solution is poured into water (200 ml.). The 2-chloro-N-[2-hydroxy-3-iodo-5-(1,1-dimethylethyl)benzyl]-acetamide which precipitates is collected, dried by suction and dissolved in ethanol (75 ml.). Concentrated hydrochloric acid (15 ml.) is added and the mixture is refluxed for two hours. The mixture is concentrated to one-half its original volume and allowed to cool. The resulting precipitate (1.4 g.), which is unhydrolyzed 2-chloro-N-[2-hydroxy-3-iodo-5-(1,1-dimethylethyl)benzyl]acetamide, is collected. The filtrate is concentrated to 25 ml. and, upon cooling, crude 2-aminomethyl-4-(1,1-dimethylethyl)-6-iodophenol hydrochloride (4 g.) separates which upon crystallization from a mixture of ethanol and ether affords substantially pure 2-aminomethyl-4-(1,1-dimethylethyl)-6-iodophenol hydrochloride (2.5 g.), m.p. 200°-201° (dec.).

1. customThe 2-chloro-N-[2-hydroxy-3-iodo-5-(1,1-dimethylethyl)benzyl]-acetamide which precipitates
2. customis collected
3. customdried by suction
4. dissolutiondissolved in ethanol (75 ml.)
5. additionConcentrated hydrochloric acid (15 ml.) is added
6. temperaturethe mixture is refluxed for two hours
7. concentrationThe mixture is concentrated to one-half its original volume
8. temperatureto cool
9. customis collected
10. concentrationThe filtrate is concentrated to 25 ml
11. temperatureand, upon cooling
12. customupon crystallization
13. additionfrom a mixture of ethanol and ether