Hydrochloric Acid → Ethyl 3-methyl-4-hydroxy-5-ethylbenzofuran-2-carboxylate

HRID 29318Notes

Reaction equation

HRID 29318 reaction equation
[C:1]([C:4]1[C:16]([OH:17])=[C:15]([CH2:18][CH3:19])[CH:14]=[CH:13][C:5]=1[O:6][CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])(=O)[CH3:2].[O-]CC.[Na+].Cl>C(O)C>[CH3:2][C:1]1[C:4]2[C:16]([OH:17])=[C:15]([CH2:18][CH3:19])[CH:14]=[CH:13][C:5]=2[O:6][C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2723922Sodium ethoxideHCID 86058897Ethyl (2-acetyl-4-ethyl-3-hydroxyphenoxy)acetate

Product 1

HCID 68711669Ethyl 3-methyl-4-hydroxy-5-ethylbenzofuran-2-carboxylateYield 50.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1.92 g (7.22 mmol) of ethyl (2-acetyl-4-ethyl-3-hydroxyphenoxy)acetate in 35 mL of absolute ethanol was added 0.54 g (7.94 mmol) of sodium ethoxide. The reaction was heated at reflux for 3 h and then cooled to room temperature, acidified with 1N HCl, and concentrated in vacuo. The residue was diluted with water and extracted with ethyl acetate. The organics were washed with water and brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was chromatographed on silica gel eluting with ethyl acetate/heaxnes (1:9) to provide 0.9 g of ethyl 3-methyl-4-hydroxy-5-ethylbenzofuran-2-carboxylate.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 3 h
  3. concentrationconcentrated in vacuo
  4. additionThe residue was diluted with water
  5. extractionextracted with ethyl acetate
  6. washThe organics were washed with water and brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue was chromatographed on silica gel eluting with ethyl acetate/heaxnes (1:9)

Sources & evidence

ORD record
ord-cdb43755c7a74799aba58892b2d7d2d1
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Reaction notes

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