Hydrochloric Acid → (2,5-Dimethoxy-4-methylphenyl)-7,7-dimethyloctan-1-one

HRID 844427

Reaktionsgleichung

Reaktionsgleichung von HRID 844427
[CH3:1][C:2]([CH3:12])([CH3:11])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]([OH:10])=O.C(Cl)(=O)C(Cl)=O.[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][C:22]=1[CH3:29].[Al+3].[Cl-].[Cl-].[Cl-].Cl>C(Cl)Cl.CN(C=O)C>[CH3:28][O:27][C:24]1[CH:23]=[C:22]([CH3:29])[C:21]([O:20][CH3:19])=[CH:26][C:25]=1[C:8](=[O:10])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][C:2]([CH3:1])([CH3:12])[CH3:11]

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 62838Versatic 10HCID 65578Oxalyl chlorideHCID 905522,5-DimethoxytolueneHCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 22612534(2,5-Dimethoxy-4-methylphenyl)-7,7-dimethyloctan-1-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideKatalysatorHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

1 g of 7,7-dimethyloctanoic acid is dissolved in 20 ml of DCM cooled to 0° C., 0.57 ml of oxalyl chloride is added and the mixture is then left stirring for 1 hour at 0° C. and for 2 hours at RT. 0.93 ml of 2,5-dimethoxytoluene and one drop of DMF are added, the mixture is cooled to 0° C., 940 mg of AlCl3 are then added and the mixture is left stirring for 1 hour at 0° C. and overnight at RT. It is poured into 10% HCl solution and extracted with ether, and the combined organic phases are then washed with 2N sodium hydroxide, dried and concentrated. The residue is chromatographed on silica, eluting with DCM/pentane (85/15; v/v) to give 1.05 g of the expected compound.

Aufarbeitung

  1. waitthe mixture is then left
  2. temperaturethe mixture is cooled to 0° C.
  3. waitthe mixture is left
  4. stirringstirring for 1 hour at 0° C. and overnight at RT
  5. extractionextracted with ether
  6. washthe combined organic phases are then washed with 2N sodium hydroxide
  7. customdried
  8. concentrationconcentrated
  9. customThe residue is chromatographed on silica
  10. washeluting with DCM/pentane (85/15; v/v)

Quellen und Nachweise

ORD-Eintrag
ord-60fc8cae1c7841cdb0b8184243239d20
Quelldatensatz
uspto-grants-2002_04
Patentnummer
US06380230B1

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