Ethylene Glycol → 3-(1,3-Dioxolan-2-yl)-6-methoxybenzofuran

HRID 273338Notes

Reaction equation

HRID 273338 reaction equation
[CH3:1][O:2][C:3]1[CH:13]=[CH:12][C:6]2[C:7]([CH:10]=[O:11])=[CH:8][O:9][C:5]=2[CH:4]=1.[OH:14][CH2:15][CH2:16]O.O>C1C=CC=CC=1>[O:11]1[CH2:16][CH2:15][O:14][CH:10]1[C:7]1[C:6]2[CH:12]=[CH:13][C:3]([O:2][CH3:1])=[CH:4][C:5]=2[O:9][CH:8]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 962WaterHCID 824109866-Methoxybenzofuran-3-carbaldehyde

Product 1

HCID 691945443-(1,3-Dioxolan-2-yl)-6-methoxybenzofuranYield 95%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 6-methoxybenzofuran-3-carbaldehyde (0.600 g, 3.41 mmol), HOCH2CH2OH (3.17 g, 51 mmol) and p-toluenesulfonic acids (0.001 g) in benzene (20 mL) was refluxed for 8 h using a Dean-Stark water trap. The mixture was concentrated under reduced pressure and then diluted with EtOAc. The organic solution was washed with water, dried over anhydrous MgSO4, and concentrated to give 3-(1,3-dioxolan-2-yl)-6-methoxybenzofuran (0.711 g, 95%)

Workup

  1. temperaturewas refluxed for 8 h
  2. concentrationThe mixture was concentrated under reduced pressure
  3. additiondiluted with EtOAc
  4. washThe organic solution was washed with water
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b85f95c64a904ebdba1cf6a4ca14aca7
Source dataset
uspto-grants-2008_11
Patent number
US07456289B2

Reaction notes

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