Trifluoroacetic acid → HCID 13006688, compound

HRID 2267970Notes

Reaction equation

HRID 2267970 reaction equation
Cl[CH2:2][CH2:3][C:4](=[O:8])[CH2:5][CH2:6]Cl.[F:9][C:10]([F:15])([F:14])[C:11]([OH:13])=[O:12].[F:16][C:17]([F:22])([F:21])[C:18]([O-:20])=[O:19].[Na+]>>[F:9][C:10]([F:15])([F:14])[C:11]([O:13][CH2:2][CH2:3][C:4](=[O:8])[CH2:5][CH2:6][O:20][C:18](=[O:19])[C:17]([F:22])([F:21])[F:16])=[O:12]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 517019Sodium TrifluoroacetateHCID 5611901,5-Dichloropentan-3-one

Product 1

HCID 13006688HCID 13006688, compound

Conditions

Temperature
75 °C

Procedure

A mixture of 17.85 g of 1,5-dichloropentan-3-one, 92 mL of trifluoroacetic acid, and 34.55 g of sodium trifluoroacetate was stirred and heated at 75° C. for 64 hours. The mixture was allowed to cool to room temperature, was poured over crushed ice, and a product of 1,5-bis(trifluoroacetoxy)pentan-3-one was extracted with dichloromethane. After drying with MgSO4, filtering, and removal of the solvent, 24.4 g of crude 1,5-bis(trifluoroacetoxy)pentan-3-one product was obtained. Analysis of the 1,5-bis(trifluoroacetoxy)pentan-3-one showed 1HNMR (CDCl3, TMS ref.): 2.94 (t, 4H), 4.63 (t, 4H) ppm.

Workup

  1. temperatureto cool to room temperature
  2. additionwas poured
  3. customover crushed ice
  4. extractiona product of 1,5-bis(trifluoroacetoxy)pentan-3-one was extracted with dichloromethane
  5. dry with materialAfter drying with MgSO4
  6. filtrationfiltering
  7. customremoval of the solvent

Sources & evidence

ORD record
ord-50c4afaac15044c1b271561fc1c9d394
Source dataset
uspto-grants-2001_12
Patent number
US06325876B1

Reaction notes

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