反応 #59518

反応方程式

3-(4-methoxyphenyl)-2-phenylpropionic acid

Thionylchloride

→

6-Methoxy-2-phenylindan-1-one

収率 67.8%

溶媒

methylenechloride

反応条件

後処理

1. 1
   その他reaction mixture
2. 2
   その他Solvent was evaporated under vacuum
3. 3
   workup.DISSOLUTIONPrecipitate was dissolved to methylenechloride
4. 4
   温度Solution was cooled to 0-3° C
5. 5
   workup.ADDITIONThis solution and aluminium chloride (2.5g) were mixed slowly over 4 hours
6. 6
   その他under 4° C
7. 7
   workup.ADDITIONAfter mixing
8. 8
   その他reaction mixture
9. 9
   workup.STIRRINGwas stirred at room temperature for 2 h
10. 10
    その他Reaction
11. 11
    その他was quenched
12. 12
    workup.ADDITIONby pouring to dilute ice cold hydrochloric acid
13. 13
    その他Layers were separated
14. 14
    抽出water solution was extracted with methylenechloride
15. 15
    洗浄Combined organic layers were washed with water
16. 16
    その他dried
17. 17
    その他evaporated
18. 18
    その他Crude product was triturated

実験手順

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).

出典