Potassium Carbonate → Methyl 3,4-methylenedioxy-5-methoxybenzoate

HRID 2420815Notes

Reaction equation

HRID 2420815 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([O:13][CH3:14])[C:11]=1[OH:12])[C:5]([O:7][CH3:8])=[O:6].[C:15]([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH3:14][O:13][C:10]1[C:11]2[O:12][CH2:15][O:1][C:2]=2[CH:3]=[C:4]([C:5]([O:7][CH3:8])=[O:6])[CH:9]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 99622m3OMG

Product 1

HCID 601780Methyl 3,4-methylenedioxy-5-methoxybenzoateYield 80%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of methyl 3,4-dihydroxy-5-methoxybenzoate (15.3 g, 0.078 mol) in acetone (500 mL) was added CH2BrCl (34.4 g, 0.27 mol) and K2CO3 (75 g, 0.54 mol) at 80° C. The resulting mixture was heated at reflux for 4 h. The mixture was cooled to room temperature and solid K2CO3 was filtered off. The filtrate was concentrated under reduced pressure, and the residue was dissolved in EtOAc (100 mL). The organic layer was washed with water, dried over anhydrous Na2SO4, and evaporated under reduced pressure to give the crude product, which was purified by column chromatography on silica gel (Petroleum Ether/Ethyl Acetate=10:1) to afford methyl 7-methoxybenzo[d][1,3]dioxole-5-carboxylate (12.6 g, 80%). 1H NMR (400 MHz, CDCl3) δ 7.32 (s, 1H), 7.21 (s, 1H), 6.05 (s, 2H), 3.93 (s, 3H), 3.88 (s, 3H).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 4 h
  3. filtrationsolid K2CO3 was filtered off
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. dissolutionthe residue was dissolved in EtOAc (100 mL)
  6. washThe organic layer was washed with water
  7. dry with materialdried over anhydrous Na2SO4
  8. customevaporated under reduced pressure
  9. customto give the crude product, which
  10. customwas purified by column chromatography on silica gel (Petroleum Ether/Ethyl Acetate=10:1)

Sources & evidence

ORD record
ord-75702b38d8d04acf9b4205f144d8c474
Source dataset
uspto-grants-2011_06
Patent number
US07956052B2

Reaction notes

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