Acetic Acid → HCID 67418330, compound

HRID 1951371Notes

Reaction equation

HRID 1951371 reaction equation
[CH:1]([C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][C:4]=1[O:11][C:12]([F:15])([F:14])[F:13])=O.[CH3:16][C:17](=[O:22])[CH2:18][C:19](=[O:21])[CH3:20].C(O)(=O)C.N1CCCCC1>ClCCl>[C:19]([C:18]([C:17](=[O:22])[CH3:16])=[CH:1][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][C:4]=1[O:11][C:12]([F:15])([F:14])[F:13])(=[O:21])[CH3:20]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 31261AcetylacetoneHCID 59186922HCID 59186922, compound

Product 1

HCID 67418330HCID 67418330, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3.32 g (15.43 mmol) of 4-formyl-3-(trifluoromethoxy)benzonitrile, 1.55 g (15.43 mmol) of 2,4-pentanedione, 1.39 g of acetic acid (23.15 mmol) and 262 mg (3.09 mmol) of piperidine are dissolved in 150 ml of dichloromethane and heated under reflux with an inverse water trap overnight. After complete conversion has been detected by a TLC check, the mixture is diluted with 100 ml of dichloromethane and washed with water and saturated sodium chloride solution. The solvent is removed in a rotary evaporator. 4.56 g (99% of theory) of crude 4-(2-acetyl-3-oxobut-1-en-1-yl)-3-(trifluoromethoxy)benzonitrile are obtained and are reacted directly without further purification.

Workup

  1. temperatureheated
  2. temperatureunder reflux with an inverse water trap overnight
  3. washwashed with water and saturated sodium chloride solution
  4. customThe solvent is removed in a rotary evaporator

Sources & evidence

ORD record
ord-161f6d299bce4fde838d9b19608509d4
Source dataset
uspto-grants-2013_03
Patent number
US08404709B2

Reaction notes

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