Sulfuric Acid → 6-Methoxy-benzofuran-2,3-dicarboxylic acid diethyl ester

HRID 1804786Notes

Reaction equation

HRID 1804786 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[CH:5]([O:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=1)[C:6](=O)[C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH3:2].S(=O)(=O)(O)O>>[CH2:1]([O:3][C:4]([C:5]1[O:13][C:14]2[CH:15]=[C:16]([O:20][CH3:21])[CH:17]=[CH:18][C:19]=2[C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:22])[CH3:2]

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 591526762-(3-Methoxy-phenoxy)-3-oxo-succinic acid diethyl ester

Product 1

HCID 591526576-Methoxy-benzofuran-2,3-dicarboxylic acid diethyl ester

Procedure

2-(3-Methoxy-phenoxy)-3-oxo-succinic acid diethyl ester (23) (60 g, 193.4 mmol) is dissolved in 32 ml of cooled (−15° C.) cone, sulfuric acid and stirred for 3 h whereas the reaction mixture slowly warmed up to room temperature. Then the mixture is poured onto 1 kg of ice and extracted with diethyl ether. The organic layers are washed with brine, dried over sodium sulfate, filtrated and evaporated. The crude product is purified by Flash-chromatography (silica gel, ethyl acetate/hexanes 1:9).

Workup

  1. extractionextracted with diethyl ether
  2. washThe organic layers are washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltrated
  5. customevaporated
  6. customThe crude product is purified by Flash-chromatography (silica gel, ethyl acetate/hexanes 1:9)

Sources & evidence

ORD record
ord-f01c316d4f3a497b9737865941191e58
Source dataset
uspto-grants-2013_01
Patent number
US08354431B2

Reaction notes

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