반응 #62738

반응 방정식

Methyl 3,4-dimethoxy-5-hydroxybenzoate

propargyl chloride

potassium carbonate

→

methyl 3,4-dimethoxy-5-(2-propynyloxy)benzoate

수율 49.0%

용매

acetone

반응 조건

후처리

1. 1
   온도cooled
2. 2
   여과filtered
3. 3
   농축concentrated
4. 4
   workup.DISSOLUTIONThe resulting oil was dissolved in ethyl acetate (20 mL)
5. 5
   세척washed with water (3×10 mL)
6. 6
   건조The organic layer was dried (Na2SO4)
7. 7
   농축concentrated

실험 절차

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 recrystllized 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.

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