Acetic Acid → 4-(2-Acetyl-3-oxobut-1-en-1-yl)-3-chlorobenzonitrile

HRID 1951394Notes

Reaction equation

HRID 1951394 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[CH:10]=O)[C:5]#[N:6].[CH3:12][C:13](=[O:18])[CH2:14][C:15](=[O:17])[CH3:16].C(O)(=O)C.N1CCCCC1>ClCCl.C1CCCCC1.C(OCC)(=O)C>[C:15]([C:14]([C:13](=[O:18])[CH3:12])=[CH:10][C:9]1[CH:8]=[CH:7][C:4]([C:5]#[N:6])=[CH:3][C:2]=1[Cl:1])(=[O:17])[CH3:16]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 31261AcetylacetoneHCID 122905503-Chloro-4-formylbenzonitrile

Product 1

HCID 674168404-(2-Acetyl-3-oxobut-1-en-1-yl)-3-chlorobenzonitrileYield 89.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 21867204Cyclohexane ethylacetateSolvent

Procedure

300 mg (1.812 mmol) of 3-chloro-4-formylbenzonitrile, 181.4 mg (1.812 mmol) of 2,4-pentanedione, 163.2 mg (2.72 mmol) of acetic acid and 30.9 mg (0.36 mmol) of piperidine are dissolved in 15 ml of dichloromethane and heated under reflux with an inverse water trap overnight. The mixture shows complete conversion (TLC check, mobile phase: cyclohexane/ethyl acetate 5:1). The mixture is diluted with dichloromethane, washed with water and saturated sodium chloride solution and dried with sodium sulfate. The solvent is removed in a rotary evaporator. 403 mg (89.8% of theory) of 4-(2-acetyl-3-oxobut-1-en-1-yl)-3-chlorobenzonitrile are obtained and are reacted 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. dry with materialdried with sodium sulfate
  5. customThe solvent is removed in a rotary evaporator

Sources & evidence

ORD record
ord-8344fbcb2ebf436692eb2bcd4f9543bb
Source dataset
uspto-grants-2013_03
Patent number
US08404709B2

Reaction notes

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