Potassium Carbonate → Methyl 3,4-dimethoxy-5-(2-propynyloxy)benzoate

HRID 280021Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 280021
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([OH:15])[C:12]=1[O:13][CH3:14])[C:6]([O:8][CH3:9])=[O:7].[CH2:16](Cl)[C:17]#[CH:18].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.[I-].[Na+]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([O:15][CH2:18][C:17]#[CH:16])[C:12]=1[O:13][CH3:14])[C:6]([O:8][CH3:9])=[O:7]

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 122213-Chloro-1-propyneHCID 2733956Methyl 3-hydroxy-4,5-dimethoxybenzoate

Produkt 1

HCID 12849835Methyl 3,4-dimethoxy-5-(2-propynyloxy)benzoateAusbeute 49 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 5238Sodium IodideKatalysatorHCID 180AcetoneLösungsmittel

Versuchsvorschrift

Methyl 3,4-dimethoxy-5-hydroxybenzoate (E. Spath and H. Roder, Mon. f. Chem. 1922, 43, 93; G. J. Kapadia, Y. N. Vaishnav, M. B. E. Fayez, J. Pharm. Sci. 1969, 9, 1157) (0.54 g, 2.54 mmol), propargyl chloride (0.23 g, 3.04 mmol), sodium iodide (3 mg, 0.02 mmol) and potassium carbonate (0.53 g, 3.81 mmol) were refluxed in acetone (10 mL) for 18 hr, cooled, filtered and concentrated. The resulting oil was dissolved in ethyl acetate (20 mL) and washed with water (3×10 mL). The organic layer was dried (Na2SO4), concentrated and recrystallized from alcohol (2.5 mL)/hexane (20 mL) to give methyl 3,4-dimethoxy-5-(2-propynyloxy)benzoate (0.29 g, 49%); mp 72°-73.5°. Anal. Calcd for C13H14O5 : C, 62.39; H, 5.64. Found: C, 62.28; H, 5.68.

Aufarbeitung

  1. temperaturecooled
  2. filtrationfiltered
  3. concentrationconcentrated
  4. dissolutionThe resulting oil was dissolved in ethyl acetate (20 mL)
  5. washwashed with water (3×10 mL)
  6. dry with materialThe organic layer was dried (Na2SO4)
  7. concentrationconcentrated
  8. customrecrystallized from alcohol (2.5 mL)/hexane (20 mL)

Quellen und Nachweise

ORD-Eintrag
ord-bf720cdd6d21469d94f2d41471a3557f
Quelldatensatz
uspto-grants-1986_05
Patentnummer
US04587342

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