Sulfuric Acid → HCID 10198445, compound

HRID 1579847Notes

Reaction equation

HRID 1579847 reaction equation
[O:1]=[C:2]1[C:6](=O)[CH2:5][C:4](=[O:8])[CH:3]1[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16].S(=O)(=O)(O)O.[H][H]>[Pd].C(O)(=O)C>[O:1]=[C:2]1[CH2:6][CH2:5][C:4](=[O:8])[CH:3]1[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16]

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 19367748HCID 19367748, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 10198445HCID 10198445, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture containing 45.7 parts of 2,3,5-trioxocyclopentaneheptanoic acid, 13 parts of 5% palladium-on-carbon catalyst, 453 parts of glacial acetic acid and 63.3 parts of concentrated sulfuric acid is shaken with hydrogen at a pressure of 3 atmospheres until 2 molecular equivalents of hydrogen are absorbed. The reaction mixture is then filtered and the resulting filtrate is mixed with 100 parts of solid sodium acetate. Evaporation of the mixture to dryness affords a solid residue which is extracted with water. The resulting extract is filtered and the filter cake is washed with water, dried, then recrystallized from acetone to afford white crystals of 2,5-dioxocyclopentaneheptanoic acid, melting at about 160°-161.5°.

Workup

  1. customare absorbed
  2. filtrationThe reaction mixture is then filtered
  3. additionthe resulting filtrate is mixed with 100 parts of solid sodium acetate
  4. customEvaporation of the mixture to dryness
  5. customaffords a solid residue which
  6. extractionis extracted with water
  7. extractionThe resulting extract
  8. filtrationis filtered
  9. washthe filter cake is washed with water
  10. customdried
  11. customrecrystallized from acetone

Sources & evidence

ORD record
ord-ab2ddea3cbb34e2ba3cc8eb5f944938c
Source dataset
uspto-grants-1976_01
Patent number
US03931411

Reaction notes

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