Hydrochloric Acid → Methyl 8-Methoxy-2,3-dihydrobenzo[b][1,4]dioxine-6-carboxylate

HRID 2230604Notes

Reaction equation

HRID 2230604 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(=O)([O-])[O-].[K+].[K+].Br[CH:22](Br)[CH3:23].Cl>CC(C)=O.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[C:11]2[O:14][CH2:23][CH2:22][O:13][C:12]=12)[C:6]([O:8][CH3:9])=[O:7]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 112011,1-DibromoethaneHCID 11430Potassium CarbonateHCID 99622m3OMG

Product 1

HCID 18464946Methyl 8-Methoxy-2,3-dihydrobenzo[b][1,4]dioxine-6-carboxylate

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

Combine methyl 3-methoxy-4,5-dihydroxybenzoate (0.5 g, 2.5 mmol) and potassium carbonate (1.74 g, 12.65 mmol) in acetone (25 mL). Add dibromoethane (2.37 g, 12.65 mmol). Heat to reflux. After 24 hours, cool in an ice bath, acidify with a 1 M aqueous hydrochloric acid solution (35 mL), add water (25 mL), and extract three times 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-ethylenedioxybenzoate.

Workup

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

Sources & evidence

ORD record
ord-44d538195e2945ae83d8a7e961f5a2d2
Source dataset
uspto-grants-2002_07
Patent number
US06423704B1

Reaction notes

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