Hydrochloric Acid → HCID 4738324, compound

HRID 430767Notes

Reaction equation

HRID 430767 reaction equation
[CH3:1][O:2][C:3]1[C:11]2[O:10][CH:9]=[C:8]([CH2:12][C:13]([O:15]C)=[O:14])[C:7]=2[CH:6]=[CH:5][CH:4]=1.[OH-].[Na+].Cl.O>CO>[CH3:1][O:2][C:3]1[C:11]2[O:10][CH:9]=[C:8]([CH2:12][C:13]([OH:15])=[O:14])[C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 11435946Methyl 2-(7-methoxybenzofuran-3-yl)acetate

Product 1

HCID 4738324HCID 4738324, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl (7-methoxy-benzofuran-3-yl)acetate (1.12 g) was dissolved in methanol (20 ml). To this solution, 2N aqueous sodium hydroxide solution (5 ml) was added and the resulting solution was stirred at room temperature for 13.5 hours. To this solution, 1N hydrochloric acid (12 ml) was added and the reaction solution was poured into water layer (200 ml), followed by extraction twice with ethyl acetate (50 ml). The organic layers were combined and washed with saturated brine, followed by drying over sodium sulfate. Sodium sulfate was removed by filtration and the solvent was removed under reduced pressure. The residue was recrystallized from hexane/chloroform to obtain the desired compound (0.95 g, yield: 91%).

Workup

  1. extractionfollowed by extraction twice with ethyl acetate (50 ml)
  2. washwashed with saturated brine
  3. dry with materialby drying over sodium sulfate
  4. customSodium sulfate was removed by filtration
  5. customthe solvent was removed under reduced pressure
  6. customThe residue was recrystallized from hexane/chloroform

Sources & evidence

ORD record
ord-3c297ee405ad4169931342fe959e72b3
Source dataset
uspto-grants-2001_11
Patent number
US06323235B1

Reaction notes

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