반응 #59518

반응 방정식

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

Thionylchloride

→

6-Methoxy-2-phenylindan-1-one

수율 67.8%

용매

methylenechloride

반응 조건

후처리

1. 1
   기타reaction mixture
2. 2
   기타Solvent was evaporated under vacuum
3. 3
   workup.DISSOLUTIONPrecipitate was dissolved to methylenechloride
4. 4
   온도Solution was cooled to 0-3° C
5. 5
   workup.ADDITIONThis solution and aluminium chloride (2.5g) were mixed slowly over 4 hours
6. 6
   기타under 4° C
7. 7
   workup.ADDITIONAfter mixing
8. 8
   기타reaction mixture
9. 9
   workup.STIRRINGwas stirred at room temperature for 2 h
10. 10
    기타Reaction
11. 11
    기타was quenched
12. 12
    workup.ADDITIONby pouring to dilute ice cold hydrochloric acid
13. 13
    기타Layers were separated
14. 14
    추출water solution was extracted with methylenechloride
15. 15
    세척Combined organic layers were washed with water
16. 16
    기타dried
17. 17
    기타evaporated
18. 18
    기타Crude product was triturated

실험 절차

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).

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