Hydrochloric Acid → Tert-butyl 3-(2-formyl-3-methylphenyl)propanoate

HRID 64425Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 64425
[OH:1][CH2:2][C:3]1[C:8]([CH3:9])=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:10][CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13].C(N(CC)CC)C.Cl.C(OCC)(=O)C>CS(C)=O>[CH:2]([C:3]1[C:8]([CH3:9])=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:10][CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[O:1]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 86713433Tert-butyl 3-[2-(hydroxymethyl)-3-methylphenyl]propanoate

Produkt 1

HCID 86713435Tert-butyl 3-(2-formyl-3-methylphenyl)propanoateAusbeute 92,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

To a solution of 770 mg of tert-butyl 3-[2-(hydroxymethyl)-3-methylphenyl]propanoate in 16 ml of dimethylsulfoxide were added 4 ml of triethylamine and 1.22 g of a sulfur trioxide pyridine complex, followed by stirring at room temperature for 5 hours. To the reaction mixture were added diluted hydrochloric acid and ethyl acetate to carry out a layer separation operation. The organic layer was sequentially washed with water, saturated aqueous sodium hydrogen carbonate solution, water, and saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 707 mg of tert-butyl 3-(2-formyl-3-methylphenyl)propanoate.

Aufarbeitung

  1. customa layer separation operation
  2. washThe organic layer was sequentially washed with water, saturated aqueous sodium hydrogen carbonate solution, water, and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-bb620d24890d4ac992089582cc8b1162
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447090B2

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