Acetic Acid → 5-Methoxy-3-methylbenzofuran

HRID 2091178Notes

Reaction equation

HRID 2091178 reaction equation
[C:1]([C:4]1[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=[CH:11][C:5]=1[O:6][CH2:7]C(O)=O)(=O)[CH3:2].C(OC(=O)C)(=O)C.C(O)(=O)C>O>[CH3:16][O:15][C:13]1[CH:12]=[CH:11][C:5]2[O:6][CH:7]=[C:1]([CH3:2])[C:4]=2[CH:14]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 7918Acetic AnhydrideHCID 13156994Acetic acid, 2-(2-acetyl-4-methoxyphenoxy)-

Product 1

HCID 131569985-Methoxy-3-methylbenzofuranYield 81.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of (2-acetyl-4-methoxyphenoxy)acetic acid (10.0 g) synthesized above, acetic anhydride (18.3 g) and acetic acid (100 mL) was stirred at 110° C. for 5 hr, poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (5% ethyl acetate/hexane) to give the title object compound (5.87 g, 81%) as a colorless oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (5% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-741101901d7541238fe4c451fc6c11a5
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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