反应详情

Aluminum chloride (26.7 g) is added to nitrobenzene (20 ml) and 4-chlorobutyric acid chloride (15.5 g) is added dropwise to the mixture with ice-cooling. Naphthalene (12.8 g) is slowly added to the mixture with ice-cooling and stirring is continued at the same temperature for 30 minutes. After stirring at room temperature for additional 2 hours, the reaction mixture is poured into ice-hydrochloric acid and extracted with chloroform. The chloroform extract is washed with water, saturated aqueous sodium bicarbonate, water and then saturated aqueous sodium chloride and dried over anhydrous sodium sulfate. The dried solution is distilled. A fraction having b.p. 187°-191° C./1.6 mmHg is separated and purified by silica gel column chromatography. The product thus obtained is crystallized from hexane and then further recrystallized from hexane-petroleum ether to obtain 2-(4-chlorobutyryl)naphthalene (4.2 g) as colorless flakes, m.p. 43°-44° C.

1. additionis added dropwise to the mixture with ice-
2. temperaturecooling
3. temperaturecooling
4. stirringAfter stirring at room temperature for additional 2 hours
5. extractionextracted with chloroform
6. extractionThe chloroform extract
7. washis washed with water, saturated aqueous sodium bicarbonate, water
8. dry with materialsaturated aqueous sodium chloride and dried over anhydrous sodium sulfate
9. distillationThe dried solution is distilled
10. customis separated
11. custompurified by silica gel column chromatography
12. customThe product thus obtained
13. customis crystallized from hexane
14. customfurther recrystallized from hexane-petroleum ether