Acetone → 1,5-Bis(4-chlorophenyl)-1,4-pentadien- 3-one

HRID 705466Notes

Reaction equation

HRID 705466 reaction equation
[CH3:1][C:2]([CH3:4])=[O:3].[Cl:5][C:6]1[CH:13]=[CH:12][C:9]([CH:10]=O)=[CH:8][CH:7]=1.[NH4+].[Cl-:15]>>[Cl:5][C:6]1[CH:13]=[CH:12][C:9](/[CH:10]=[CH:1]/[C:2](=[O:3])/[CH:4]=[CH:10]/[C:9]2[CH:12]=[CH:13][C:6]([Cl:15])=[CH:7][CH:8]=2)=[CH:8][CH:7]=1

Participants

4

Reactant 3

HCID 180AcetoneHCID 77264-ChlorobenzaldehydeHCID 25517Ammonium Chloride

Product 1

HCID 53785841,5-Bis(4-chlorophenyl)-1,4-pentadien- 3-oneYield 34%

Procedure

A mixture of LiClO4 (1.2 g, 11 mmol), acetone (418 μL, 5.7 mmol) and 4-chloro-benzaldehyde (1.6 g, 11 mmol) was treated with TEA (159 μL, 1.1 mmol) and stirred for 4 min at ambient temperature. A saturated aq. NH4Cl solution was added to the reaction mixture and extracted with CH2Cl2. The combined organic layers were dried with MgSO4, filtered and the solvent was removed in vacuo. The residue was recrystallized from CH2Cl2 to obtain NW308 as yellow crystals (586 mg, 34%). mp: 182-184° C. 1H NMR (300 MHz, CDCl3) δ (ppm): 7.60 (d, 3J=15.9 Hz, 2H, Hvin), 7.46 (d, 3J=8.5 Hz, 4H, HAr), 7.31 (d, 3J=8.5 Hz, 4H, HAr), 6.95 (d, 3J=15.9 Hz, 2H, Hvin). 13C NMR (75 MHz, CDCl3) δ (ppm): 188.3 (C), 142.0 (CH), 136.5 (C), 133.2 (C), 129.51 (CH), 129.2 (CH). MS (FAB) m/z: 303.1 (M+). Anal. calcd for C17H12Cl2O: C, 67.35; H, 3.99; Cl, 23.39. Found: C, 67.33; H, 4.01; Cl, 23.17%.

Workup

  1. extractionextracted with CH2Cl2
  2. dry with materialThe combined organic layers were dried with MgSO4
  3. filtrationfiltered
  4. customthe solvent was removed in vacuo
  5. customThe residue was recrystallized from CH2Cl2

Sources & evidence

ORD record
ord-a838035abaf14858b4e86f534a2103b4
Source dataset
uspto-grants-2015_11
Patent number
US09174960B2

Reaction notes

Loading…