反应详情

To a cold (−10° C., brine/ice cooling bath) stirred mixture of 5.43 g (28.2 mmol) of 9-methylanthracene and oxalyl chloride (13.50 mL, 159.5 mmol) in CS2 (60 mL) was added aluminium chloride (6.0 g, 45 mmol). The solution changed from a red-orange colour to a very intense dark crimson colour and vigorous effervescence was observed (hydrogen chloride) and an exotherm occurred raising the reaction temperature from −10° C. to −4° C. After a few minutes stirring the exotherm eased off and an intense dark red tar deposited from the solution which lightened to a yellow colour, the reaction mixture was then stirred cold for a period of 2 hours. After 2 hours, additional CS2 (60 mL) and aluminium chloride (4.5 g, 33.7 mmol) were added, and stirring was continued for 2 hours at 0° C. and then overnight at room temperature. HCl (2M, aq, 150 mL) was then added to the reaction mixture [NOTE: Extreme caution, very exothermic reaction ensues that causes vigorous reflux of reaction solvent], the reaction mixture was then stirred vigorously for 2 hours (large egg-shaped magnetic stirrer follower stirred at 1250 rpm) to decompose the dark red tar to an orange precipitate which was then collected by filtration, washed with water (2×150 mL), and then digested well with 300 mL of 5% NaOH(aq) for a period of 1 hour. The insoluble solids were collected by filtration, washed with water (2×50 mL), and dried in vacuo in a vacuum oven (oil immersion pump) to constant mass (22 hours). Yield: 2.411 g (34.7%, pale orange powder).

1. temperaturean exotherm occurred raising the reaction temperature from −10° C. to −4° C
2. stirringthe reaction mixture was then stirred cold for a period of 2 hours
3. stirringstirring
4. waitwas continued for 2 hours at 0° C.
5. customovernight
6. customat room temperature
7. customExtreme caution, very exothermic reaction
8. temperaturethat causes vigorous reflux of reaction solvent], the reaction mixture
9. stirringwas then stirred vigorously for 2 hours
10. stirring(large egg-shaped magnetic stirrer follower stirred at 1250 rpm)
11. filtrationwas then collected by filtration
12. washwashed with water (2×150 mL)
13. waitdigested well with 300 mL of 5% NaOH(aq) for a period of 1 hour
14. filtrationThe insoluble solids were collected by filtration
15. washwashed with water (2×50 mL)
16. customdried in vacuo in a vacuum oven (oil immersion pump) to constant mass (22 hours)