Water → Methyl-7-methoxy-2-methylbenzo[b]furan-4-carboxylate

HRID 1091832Notes

Reaction equation

HRID 1091832 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[O:9][C:10]([CH3:12])=[CH:11][C:7]=2[C:6]([C:13]([OH:15])=[O:14])=[CH:5][CH:4]=1.[C:16](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O.O>CC(C)=O>[CH3:16][O:14][C:13]([C:6]1[C:7]2[CH:11]=[C:10]([CH3:12])[O:9][C:8]=2[C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)=[O:15]

Participants

6

Reactant 4

HCID 962WaterHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 220095237-Methoxy-2-methylbenzo[b]furan-4-carboxylic acid

Product 1

HCID 66592954Methyl-7-methoxy-2-methylbenzo[b]furan-4-carboxylateYield 75%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a well stirred suspension of 7-methoxy-2-methylbenzo[b]furan-4-carboxylic acid (from step 4) (4.5 g, 24.21 mmol) and powdered potassium carbonate (7.5 g, 54.61 mmol) in acetone (740.0 mL) was added dimethyl sulfate (4.1 g, 32.76 mmol) and refluxed for 2-3 hours. Reaction mixture was cooled to room temperature and water (500 mL) was added to it. The organic material separated was extracted with ethyl acetate (3×100 ml). The combined organic layers were washed with water ((2×100 mL) and dried over anhydrous sodium sulfate. Removal of solvent under vacuo gave product (4.0 g) as brown viscous oil.

Workup

  1. temperaturerefluxed for 2-3 hours
  2. customReaction mixture
  3. customThe organic material separated
  4. extractionwas extracted with ethyl acetate (3×100 ml)
  5. washThe combined organic layers were washed with water ((2×100 mL)
  6. dry with materialdried over anhydrous sodium sulfate
  7. customRemoval of solvent under vacuo

Sources & evidence

ORD record
ord-7f2e22824d464454a068d0dc023c3e5d
Source dataset
uspto-grants-2012_03
Patent number
US08129401B2

Reaction notes

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