Water → HCID 21995833, compound

HRID 1978763Notes

Reaction equation

HRID 1978763 reaction equation
CO[CH:3](OC)[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][CH3:15])=[CH:8][CH:7]=1.O>C1(C)C=CC=CC=1>[CH2:13]([O:12][C:9]1[CH:8]=[CH:7][C:6]2[O:5][CH:4]=[CH:3][C:11]=2[CH:10]=1)[CH2:14][CH3:15]

Participants

4

Reactant 2

HCID 962WaterHCID 66221249HCID 66221249, compound

Product 1

HCID 21995833HCID 21995833, compoundYield 46.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a suspension of polyphosphoric acid (5.2 g) in toluene (120 ml) was added 4-(2,2-dimethoxy)ethoxy-propoxybenzene (5.0 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 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-propoxybenzofuran (1.7 g).

Workup

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

Sources & evidence

ORD record
ord-8e0738871bbc4fefaec5430410a63863
Source dataset
uspto-grants-2001_05
Patent number
US06235771B1

Reaction notes

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