Benzaldehyde → HCID 53901616, compound

HRID 343073Notes

Reaction equation

HRID 343073 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10](=[O:13])[CH2:11][CH3:12])=[CH:5][CH:4]=1.[CH:14](=O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.N1CCCCC1>C1(C)C=CC=CC=1>[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:10](=[O:13])[CH2:11][CH3:12])=[CH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 8082PiperidineHCID 20397081HCID 20397081, compound

Product 1

HCID 53901616HCID 53901616, compoundYield 61.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 1-(4-methylthiophenyl)-2-butanone from Step 2 (9.74 g, 50 mmol), benzaldehyde (5.85 g, 55 mmol) and piperidine (0.5 mL) in toluene (200 mL) was heated at reflux with a Dean-Stark trap for 16 hours. The mixture was cooled and solvent was removed in vacuo. The residue was partitioned between dichloromethane and water. The organic layer was washed successively with saturated ammonium chloride solution, water and brine, dried over magnesium sulfate, filtered and the filtrate was concentrated in vacuo. The crude pentenone was recrystallized from ethyl acetate and hexane to give 8.64 g of 2-(4-methylthiophenyl)-1-phenyl-1-pentene-3-one (60%) as light yellow crystals: mp 98°-99° C. Anal. Calc'd. for C18H18OS: C, 76.56; H, 6.42; N, 11.35. Found: C, 76.58; H, 6.17; N, 11.35.

Workup

  1. temperaturewas heated
  2. temperatureat reflux with a Dean-Stark trap for 16 hours
  3. temperatureThe mixture was cooled
  4. customsolvent was removed in vacuo
  5. customThe residue was partitioned between dichloromethane and water
  6. washThe organic layer was washed successively with saturated ammonium chloride solution, water and brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationthe filtrate was concentrated in vacuo
  10. customThe crude pentenone was recrystallized from ethyl acetate and hexane

Sources & evidence

ORD record
ord-6e6844868aa34a60bcc14977e9d8e91e
Source dataset
uspto-grants-1999_01
Patent number
US05859257

Reaction notes

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