Adipic Acid → 6-Oxohexanoic acid

HRID 1020968Notes

Reaction equation

HRID 1020968 reaction equation
[N+](=C)=[N-].C1(C2C=CC=CC=2)C=CC=CC=1.[C:16](O)(=[O:24])[CH2:17][CH2:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22]>>[O:24]=[CH:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22]

Participants

4

Reactant 3

HCID 196Adipic AcidHCID 7095BiphenylHCID 9550Diazomethane

Product 1

HCID 4409186-Oxohexanoic acidYield 18%

Procedure

After the reaction, the autoclave was cooled with ice, and the pressure was reduced; subsequently, the contents were treated with diazomethane, and the reaction mixture was analyzed by gas chromatography using biphenyl as an internal standard. The results confirmed that adipic acid was obtained in a yield of 38%, and 6-oxohexanoic acid was obtained in a yield of 18%. With regard to the products, the reaction mixture was analyzed by FT-NMR using coumarin as an internal standard, and the results confirmed that adipaldehyde was obtained in a yield of 42%, and adipic acid was obtained in a yield of 19%.

Workup

  1. customAfter the reaction
  2. temperaturethe autoclave was cooled with ice
  3. customwas obtained in a yield of 38%

Sources & evidence

ORD record
ord-fe4da990362f450fa2abb00a2ff0045d
Source dataset
uspto-grants-2014_05
Patent number
US08716501B2

Reaction notes

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