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

HRID 1951395Notes

Reaction equation

HRID 1951395 reaction equation
[CH3:1][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>[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[CH3:1])(=[O:17])[CH3:16]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 31261AcetylacetoneHCID 109096954-Formyl-3-methylbenzonitrile

Product 1

HCID 596030304-(2-Acetyl-3-oxobut-1-en-1-yl)-3-methylbenzonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

950 mg (6.54 mmol) of 3-methyl-4-formylbenzonitrile [S. Levesque et al., Bioorg. Med. Chem. Lett. 11, 3161-3164 (2000], 655.2 mg (6.544 mmol) of 2,4-pentanedione, 589.5 mg (9.82 mmol) of acetic acid and 111.5 mg (1.31 mmol) of piperidine are dissolved in 35 ml of dichloromethane and heated under reflux with an inverse water trap overnight. Cooling is followed by washing twice with water, and the organic phase is dried with magnesium sulfate. The solvent is removed in a rotary evaporator and the residue is purified by column chromatography (silica gel, mobile phase: initially dichloromethane, then isohexane/ethyl acetate 3:1). After concentration of the product fractions, the residue is crystallized from diethyl ether and dried under high vacuum. 1.12 g (75.3% of theory) of the title compound are obtained.

Workup

  1. temperatureheated
  2. temperatureunder reflux with an inverse water trap overnight
  3. temperatureCooling
  4. washby washing twice with water
  5. dry with materialthe organic phase is dried with magnesium sulfate
  6. customThe solvent is removed in a rotary evaporator
  7. customthe residue is purified by column chromatography (silica gel, mobile phase
  8. customAfter concentration of the product fractions, the residue is crystallized from diethyl ether
  9. customdried under high vacuum

Sources & evidence

ORD record
ord-ffc25bb006974dd58b30decbfe449b09
Source dataset
uspto-grants-2013_03
Patent number
US08404709B2

Reaction notes

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