Methane, dichloromethoxy- → Ethyl 2-(4-Formylphenyl)-2-Methylpropionate

HRID 582810Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 582810
[C:1]1([C:7]([CH3:14])([CH3:13])[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:15][O:16]C(Cl)Cl.S(=O)(O)[O-].[Na+]>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[CH:15]([C:4]1[CH:5]=[CH:6][C:1]([C:7]([CH3:13])([CH3:14])[C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:2][CH:3]=1)=[O:16]

Komponenten

6

Edukt 3

HCID 21004Methane, dichloromethoxy-HCID 232036Benzeneacetic acid, alpha,alpha-dimethyl-, ethyl esterHCID 23665763Sodium Bisulfite

Produkt 1

HCID 10966041Ethyl 2-(4-Formylphenyl)-2-Methylpropionate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24193Titanium TetrachlorideKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

Ethyl 2-phenyl-2-methylpropionate (10 g) was dissolved in 50 mL of dichloromethane and cooled to 5° C. Titanium tetrachloride (10.5 mL) and 1,1-dichloromethyl methyl ether (7.5 mL) were added and the mixture was stirred at room temperature for 60 hours. The resulting dark solution was diluted with 50 mL of dichloromethane and washed twice with 50 mL of water. The organic solution was concentrated to give an oil which was treated with 30 mL of saturated aqueous sodium bisulfite solution for 12 hours. The precipitate was collected by filtration, washed with hexane, suspended in ethyl acetate and treated with excess potassium carbonate. The organic phase was separated, dried with sodium sulfate and stripped to provide 2 g of product.

Aufarbeitung

  1. washwashed twice with 50 mL of water
  2. concentrationThe organic solution was concentrated
  3. customto give an oil which
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with hexane
  6. additiontreated with excess potassium carbonate
  7. customThe organic phase was separated
  8. dry with materialdried with sodium sulfate

Quellen und Nachweise

ORD-Eintrag
ord-8f832a4970ef4823a5210d0b24853476
Quelldatensatz
uspto-grants-1999_07
Patentnummer
US05925761

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