反应详情

温度

40 °C

To solution of 3-(4-methoxyphenyl)-2-phenylpropionic acid (4.6 g) in dry methylenechloride (26 ml) was added two drops of dry DMF. Thionylchloride (3 ml) was added and reaction mixture was stirred at 40° C. for 4 h. Solvent was evaporated under vacuum. Precipitate was dissolved to methylenechloride. Solution was cooled to 0-3° C. This solution and aluminium chloride (2.5g) were mixed slowly over 4 hours keeping temperature under 4° C. After mixing reaction mixture was stirred at room temperature for 2 h. Reaction was quenched by pouring to dilute ice cold hydrochloric acid. Layers were separated and water solution was extracted with methylenechloride. Combined organic layers were washed with water, dried and evaporated. Crude product was triturated to give 2.9 g of 6-Methoxy-2-phenylindan-1-one. 1H-NMR (400 MHz, d6-DMSO): 7.56 (d, 1H), 7.35-7.23 (m, 4H), 7.18-7.13 (m, 3H), 4.02 (dd, 1H, J 3.9, 8.0 Hz), 3.82 (s, 3H), 3.61 (dd, 1H, J 8.0, 17.2 Hz), 3.11 (dd, 1H, J 3.9, 17.2 Hz).

1. customreaction mixture
2. customSolvent was evaporated under vacuum
3. dissolutionPrecipitate was dissolved to methylenechloride
4. temperatureSolution was cooled to 0-3° C
5. additionThis solution and aluminium chloride (2.5g) were mixed slowly over 4 hours
6. customunder 4° C
7. additionAfter mixing
8. customreaction mixture
9. stirringwas stirred at room temperature for 2 h
10. customReaction
11. customwas quenched
12. additionby pouring to dilute ice cold hydrochloric acid
13. customLayers were separated
14. extractionwater solution was extracted with methylenechloride
15. washCombined organic layers were washed with water
16. customdried
17. customevaporated
18. customCrude product was triturated