Oxalic Acid → Hedione

HRID 1373499Notes

Reaction equation

HRID 1373499 reaction equation
[C:1](O)(=O)[C:2]([OH:4])=[O:3].O[CH:8]([CH:13]1[CH2:17][CH2:16][CH2:15][C:14]1=[O:18])[CH2:9][CH2:10][CH2:11][CH3:12].[CH:19](=C1CCCC1=O)CCCC>>[O:18]=[C:14]1[CH2:15][CH2:16][CH:17]([CH2:1][C:2]([O:4][CH3:19])=[O:3])[CH:13]1[CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

4

Reactant 3

HCID 971Oxalic AcidHCID 860002-PentylidenecyclopentanoneHCID 162060Cyclopentanone, 2-(1-hydroxypentyl)-

Product 1

HCID 102861Hedione

Procedure

The reaction in Comparative Example 1 was carried out 3 times, the product was distilled to recover cyclopentanone and water, then 0.0206 mol oxalic acid was added to 1.11 mol 2-(1-hydroxy-n-pentyl)cyclopentanone and 0.012 mol 2-pentylidene cyclopentanone from the product, and the mixture was reacted at 120° C. Thereafter, the reaction was carried out in the same manner as in Example 7, to give methyl 3-oxo-2-pentylcyclopentylacetate. As a result, the yield in the whole process was 28%.

Workup

  1. customThe reaction in Comparative Example 1
  2. distillationthe product was distilled
  3. customto recover cyclopentanone and water
  4. customthe mixture was reacted at 120° C

Sources & evidence

ORD record
ord-b92483900ede46188e7a2cbdc6390ddd
Source dataset
uspto-grants-2007_01
Patent number
US07161041B2

Reaction notes

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