Water → 5-Methoxybenzofuran

HRID 1978765Notes

Reaction equation

HRID 1978765 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH2:10][CH:11](OC)OC)=[CH:5][CH:4]=1.O>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:9][CH:10]=[CH:11][C:7]=2[CH:8]=1

Participants

4

Reactant 2

HCID 962WaterHCID 110244p-(2,2-Dimethoxyethoxy)anisole

Product 1

HCID 259435-MethoxybenzofuranYield 24.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a suspension of polyphosphoric acid (38.3 g) in toluene (400 ml) was added 4-methoxy-(2,2-dimethoxy)ethoxybenzene (38.0 g), and the mixture was stirred at 100° C. overnight and cooled. To the mixture was added water, and the mixture was separated. The organic layer was washed with 1N sodium hydroxide solution and then washed with saturated brine, and dried with magnesium sulfate. Under reduced pressure, the solvent was evaporated, and the residue was purified with silica gel column chromatography to give brown oil of 5-methoxybenzofuran (6.5 g).

Workup

  1. temperaturecooled
  2. customthe mixture was separated
  3. washThe organic layer was washed with 1N sodium hydroxide solution
  4. washwashed with saturated brine
  5. dry with materialdried with magnesium sulfate
  6. customUnder reduced pressure, the solvent was evaporated
  7. customthe residue was purified with silica gel column chromatography

Sources & evidence

ORD record
ord-e1ba364eb10c41cda21078f2b7c2c28c
Source dataset
uspto-grants-2001_05
Patent number
US06235771B1

Reaction notes

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