Hydrochloric Acid → Methyl 3,4-methylenedioxy-5-methoxybenzoate

HRID 2230602Notes

Reaction equation

HRID 2230602 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([OH:14])[C:12]=1[OH:13])[C:6]([O:8][CH3:9])=[O:7].[C:15](=O)([O-])[O-].[K+].[K+].ICI.Cl>CC(C)=O.CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[C:11]2[O:14][CH2:15][O:13][C:12]=12)[C:6]([O:8][CH3:9])=[O:7]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6346DiiodomethaneHCID 11430Potassium CarbonateHCID 99622m3OMG

Product 1

HCID 601780Methyl 3,4-methylenedioxy-5-methoxybenzoate

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

Combine methyl 3-methoxy-4,5-dihydroxybenzoate (0.93 g, 4.6 mmol) and potassium carbonate (3.2 g, 23.4 mmol) in acetone (25 mL) and dimethylformamide (25 mL). Add diiodomethane (6.3 g, 23.3 mmol). Heat to reflux. After 24 hours, cool in an ice bath, acidify with a 1 M aqueous hydrochloric acid solution (35 mL), and extract twice with ethyl acetate. Combine the organic layers and extract with brine. Dry over MgSO4, filter, and concentrate in vacuo to give methyl 3-methoxy-4,5-methylenedioxybenzoate.

Workup

  1. temperatureHeat to reflux
  2. temperaturecool in an ice bath
  3. extractionextract twice with ethyl acetate
  4. extractionextract with brine
  5. dry with materialDry over MgSO4
  6. filtrationfilter
  7. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-4cf05f23233f4ce1b9d8efd2080156be
Source dataset
uspto-grants-2002_07
Patent number
US06423704B1

Reaction notes

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