Methyl 4-((2,2-dimethoxy)ethoxy)benzoate → Methyl 1-benzofuran-5-carboxylate

HRID 1699848Notes

Reaction equation

HRID 1699848 reaction equation
CO[CH:3](OC)[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][CH:7]=1>ClCCCl>[CH3:13][O:12][C:10]([C:9]1[CH:14]=[CH:15][C:6]2[O:5][CH:4]=[CH:3][C:7]=2[CH:8]=1)=[O:11]

Participants

3

Reactant 1

HCID 22388309Methyl 4-((2,2-dimethoxy)ethoxy)benzoate

Product 1

HCID 12674941Methyl 1-benzofuran-5-carboxylateYield 11.7%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Methyl 4-((2,2-dimethoxy)ethoxy)benzoate (10.00 g) and polyphosphoric acid (20.00 g) were refluxed in 1,2-dichloroethane (50 ml) for 1 hr. After cooling, ice was added, and the separated organic layer was washed with 10% hydrochloric acid. The mixture was dried over magnesium sulfate, concentrated and purified by column chromatography to give the objective compound (0.86 g).

Workup

  1. temperatureAfter cooling
  2. additionice was added
  3. washthe separated organic layer was washed with 10% hydrochloric acid
  4. dry with materialThe mixture was dried over magnesium sulfate
  5. concentrationconcentrated
  6. custompurified by column chromatography

Sources & evidence

ORD record
ord-9ee082b31266429c9c46116b2d45c5c6
Source dataset
uspto-grants-2002_02
Patent number
US06348474B1

Reaction notes

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