Thionyl Chloride → 2-(2,4-Dimethoxyphenyl)-1-(2,4,6-trimethoxyphenyl)ethan-1-one

HRID 1357057

Reaktionsgleichung

Reaktionsgleichung von HRID 1357057
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[CH2:11][C:12]([OH:14])=O.O=S(Cl)Cl.[CH3:19][O:20][C:21]1[CH:26]=[C:25]([O:27][CH3:28])[CH:24]=[C:23]([O:29][CH3:30])[CH:22]=1.[Al+3].[Cl-].[Cl-].[Cl-]>C(Cl)Cl.CN(C=O)C.ClC(Cl)C>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[CH2:11][C:12]([C:22]1[C:23]([O:29][CH3:30])=[CH:24][C:25]([O:27][CH3:28])=[CH:26][C:21]=1[O:20][CH3:19])=[O:14]

Komponenten

8

Edukt 4

HCID 24386Thionyl ChlorideHCID 693011,3,5-TrimethoxybenzeneHCID 3505552-(2,4-Dimethoxyphenyl)acetic acidHCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 185054532-(2,4-Dimethoxyphenyl)-1-(2,4,6-trimethoxyphenyl)ethan-1-oneAusbeute 47,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228DimethylformamideKatalysatorHCID 6344DichloromethaneLösungsmittelHCID 63651,1-DichloroethaneLösungsmittel

Versuchsvorschrift

A solution of 2,4-dimethoxyphenyl acetic acid (7.9 g, 38 mmol) in CH2Cl2 (50 mL) plus a few drops of DMF was treated with SOCl2 (5.0 mL, 76 mmol) and the reaction was allowed to stir for 3 h at rt. The reaction mixture was then concentrated and taken up in a small amount of dichloroethane and added dropwise, at 0° C., to a solution of 1,3,5-trimethoxybenzene (12.8 g, 76 mmol) and AlCl3 (7.3 g, 57 mmol) in 50 mL dichloroethane. After 20 minutes at 0° C., the reaction was carefully quenched with 2 N HCl aq. The organic layer was separated, dried over MgSO4, filtered and concentrated to give a dark oil which was chromatographed on SiO2 (3:7 EtOAc/hexanes to 1:1 EtOAc/hexanes) to yield the desired product as a white solid (6.2 g): Mp 109-111° C.; 1H NMR (CDCl3) δ 7.06 (d, 1H, J=8.1 Hz), 6.41 (dd, 1H, J=8.1Hz, 2.4Hz), 6.39 (d, 1H, J=2.4Hz), 6.04 (s, 2H), 3.97 (s, 2H), 3.80 (s, 3H), 3.78 (s, 3H), 3.74 (s, 6H), 3.71 (s, 3H); MS FI 347 (M+H)+.

Aufarbeitung

  1. concentrationThe reaction mixture was then concentrated
  2. waitAfter 20 minutes at 0° C.
  3. customthe reaction was carefully quenched with 2 N HCl aq. The organic layer
  4. customwas separated
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a dark oil which
  9. customwas chromatographed on SiO2 (3:7 EtOAc/hexanes to 1:1 EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-6bbbc90096f64b8b90c36ede9ced585e
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06589980B2

Verknüpfte Notizen

Wird geladen…