Sulfuric Acid → HCID 19382374, compound

HRID 227824Notes

Reaction equation

HRID 227824 reaction equation
[C:1]([C:9]1[CH:13]=[CH:12][O:11][C:10]=1[C:14](NC(C)(C)C)=[O:15])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(=O)(=O)(O)[OH:22]>O1CCOCC1.O>[C:1]([C:9]1[CH:13]=[CH:12][O:11][C:10]=1[C:14]([OH:15])=[O:22])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 1118Sulfuric Acid2×HCID 66731474HCID 66731474, compound

Product 1

HCID 19382374HCID 19382374, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

To slurry of 3-benzoyl-N-tert-butylfuran-2-carboxamide (0.863 g, 3.18 mmol) in 4 mL dioxane and 3 mL water was added sulfuric acid (1.02 ml, 19.1 mmol). The mixture was sealed and heated to 120° C. for a total of 48 h. Additional 3.0 equiv H2SO4 was added, and the reaction was heated for 8 h. The reaction was cooled and partitioned between water and DCM. The aqueous layer was extracted with DCM (4×), and the combined organics were dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to give 3-benzoylfuran-2-carboxylic acid as a brown semi-solid. This material was carried on without further purification. MS m/z=217 [M+H]+. Calc'd for C12H8O4: 216.2.

Workup

  1. customThe mixture was sealed
  2. temperaturethe reaction was heated for 8 h
  3. temperatureThe reaction was cooled
  4. custompartitioned between water and DCM
  5. extractionThe aqueous layer was extracted with DCM (4×)
  6. dry with materialthe combined organics were dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-33230fc63a0946bbbf08917d00644bbe
Source dataset
uspto-grants-2009_07
Patent number
US07560551B2

Reaction notes

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