Hydrochloric Acid → 6-Methoxy-2-methylbenzofuran-3-carbaldehyde

HRID 273340Notes

Reaction equation

HRID 273340 reaction equation
Cl.[O:2]1CCO[CH:3]1[C:7]1[C:11]2[CH:12]=[CH:13][C:14]([O:16][CH3:17])=[CH:15][C:10]=2[O:9][C:8]=1[CH3:18]>C1COCC1>[CH3:17][O:16][C:14]1[CH:13]=[CH:12][C:11]2[C:7]([CH:3]=[O:2])=[C:8]([CH3:18])[O:9][C:10]=2[CH:15]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 691942533-[1,3]Dioxolan-2-yl-6-methoxy-2-methyl-benzofuran

Product 1

HCID 866061886-Methoxy-2-methylbenzofuran-3-carbaldehydeYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2N HCl (5 mL) was added to 3-[1,3]dioxolan-2-yl-6-methoxy-2-methyl-benzofuran in THF (5 mL) at 0° C. After stirring for 1 h at room temperature, the solvent was removed under reduced pressure. The residue was dissolved in EtOAc and washed with saturated NaHCO3. The aqueous layer was extracted with EtOAc (3×20 mL). The organic layers were combined and dried over anhydrous MgSO4. After the solvent was removed, the residue was purified on a silica gel column eluting with EtOAc/hexane (1:9) to give 6-methoxy-2-methylbenzofuran-3-carbaldehyde (0.090 g, 81%).

Workup

  1. customthe solvent was removed under reduced pressure
  2. dissolutionThe residue was dissolved in EtOAc
  3. washwashed with saturated NaHCO3
  4. extractionThe aqueous layer was extracted with EtOAc (3×20 mL)
  5. dry with materialdried over anhydrous MgSO4
  6. customAfter the solvent was removed
  7. customthe residue was purified on a silica gel column
  8. washeluting with EtOAc/hexane (1:9)

Sources & evidence

ORD record
ord-ffd0ed48999a4c6386934c56f12c0b3c
Source dataset
uspto-grants-2008_11
Patent number
US07456289B2

Reaction notes

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