Hydrochloric Acid → 2-Pentylcyclopentane-1,3-dione

HRID 599717Notes

Reaction equation

HRID 599717 reaction equation
[C:1]([OH:8])(=O)[CH2:2][CH2:3][C:4](O)=[O:5].Cl.[C:10](Cl)(=O)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]C>>[CH2:11]([CH:10]1[C:4](=[O:5])[CH2:3][CH2:2][C:1]1=[O:8])[CH2:12][CH2:13][CH2:14][CH3:15]

Participants

4

Reactant 3

HCID 313Hydrochloric Acid2×HCID 1110Succinic AcidHCID 17313Heptanoyl chloride2×

Product 1

HCID 109428402-Pentylcyclopentane-1,3-dione

Conditions

Temperature
80 °C

Procedure

After charging succinic acid, the mixture was allowed stand to complete generation of HCl gas. Then, thereto was added 60 g (0.4 mol) of heptanoyl chloride, and the resulting mixture was heated at 80° C. for 8 hours. Since heptanoyl chloride is also fuming (HCl gas), measures were taken against corrosion of equipment in the peripheral environment at the time of weighing, but it was with difficulty. The mixture was cooled, poured onto 60 g of ice, and maintained at −10° C. for 10 hours, depositing a product as a solid. The product was subjected to suction filtration, washed with 10% NaCl water and toluene (20 ml×3 times), and dried, yielding 8.4 g (0.05 mol) of 2-pentyl-1,3-cyclopentanedione (a compound in which R1 represents an n-pentyl group in the above formula (3)). Yields were 20.8%, 50.0%, and 12.5% relative to AlCl3, succinic acid, and heptanoyl chloride, respectively. Simultaneously, wastewater containing a large amount of an aluminum-based and a chlorine-based compound was byproduced.

Workup

  1. temperatureThe mixture was cooled
  2. temperaturemaintained at −10° C. for 10 hours
  3. filtrationThe product was subjected to suction filtration
  4. washwashed with 10% NaCl water and toluene (20 ml×3 times)
  5. customdried

Sources & evidence

ORD record
ord-e1246dbbaf2e437e91fe92164f5cd93e
Source dataset
uspto-grants-2011_03
Patent number
US07897802B2

Reaction notes

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