Hydrochloric Acid → Ethyl 4-hydroxybenzofuran-6-carboxylate

HRID 922439Notes

Reaction equation

HRID 922439 reaction equation
C([O:4][C:5]1[C:10]2[CH:11]=[CH:12][O:13][C:9]=2[CH:8]=[C:7]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:6]=1)(=O)C.C(=O)([O-])[O-].[K+].[K+].Cl>C(O)C>[OH:4][C:5]1[C:10]2[CH:11]=[CH:12][O:13][C:9]=2[CH:8]=[C:7]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 675451626-Benzofurancarboxylic acid, 4-(acetyloxy)-, ethyl ester

Product 1

HCID 11344757Ethyl 4-hydroxybenzofuran-6-carboxylateYield 95.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of the compound obtained in the above (1) (24.7 g) in ethanol (150 mL) was added potassium carbonate (42.0 g), and the mixture was heated to reflux for 30 minutes. The reaction mixture was ice-cooled, and then acidified by 10% hydrochloric acid, and then extracted with ethyl acetate. The organic layer was washed with saturated saline, dried over sodium sulfate, and then concentrated under reduced pressure. The resulting residue was triturated with n-hexane-dichloromethane (5:1) to give ethyl 4-hydroxy-1-benzofuran-6-carboxylate [REx(7-1)] (19.6 g) as a pale yellow powder.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 30 minutes
  3. temperaturecooled
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with saturated saline
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting residue was triturated with n-hexane-dichloromethane (5:1)

Sources & evidence

ORD record
ord-3593af004da64766a74ae4905e6e0957
Source dataset
uspto-grants-2016_03
Patent number
US09278944B2

Reaction notes

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