Thionyl Chloride → 6-Methoxy-2-phenylindan-1-one

HRID 1455038

Reaktionsgleichung

Reaktionsgleichung von HRID 1455038
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH:10]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:11]([OH:13])=O)=[CH:5][CH:4]=1.S(Cl)(Cl)=O>C(Cl)Cl.CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:6]([CH2:9][CH:10]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:11]2=[O:13])=[CH:7][CH:8]=1

Komponenten

5

Edukt 2

HCID 24386Thionyl ChlorideHCID 977393-(4-Methoxyphenyl)-2-phenylpropionic acid

Produkt 1

HCID 224653766-Methoxy-2-phenylindan-1-oneAusbeute 67,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideKatalysatorHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

To solution of 3-(4-methoxyphenyl)-2-phenylpropionic acid (4.6 g) in dry methylene chloride (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 methylene chloride. Solution was cooled to 0-3° C. This solution and aluminium chloride (2.5 g) 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 methylene chloride. 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).

Aufarbeitung

  1. customreaction mixture
  2. customSolvent was evaporated under vacuum
  3. dissolutionPrecipitate was dissolved to methylene chloride
  4. temperatureSolution was cooled to 0-3° C
  5. additionThis solution and aluminium chloride (2.5 g) 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 methylene chloride
  15. washCombined organic layers were washed with water
  16. customdried
  17. customevaporated
  18. customCrude product was triturated

Quellen und Nachweise

ORD-Eintrag
ord-487dc2444aa6400380ad58a24716f521
Quelldatensatz
uspto-grants-2009_01
Patentnummer
US07482340B2

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