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

HRID 280021Notes

Reaction equation

HRID 280021 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 5238Sodium IodideCatalystHCID 180AcetoneSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-bf720cdd6d21469d94f2d41471a3557f
Source dataset
uspto-grants-1986_05
Patent number
US04587342

Reaction notes

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