Benzene → HCID 118366098, compound

HRID 1479685Notes

Reaction equation

HRID 1479685 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:11]C)[CH:10]=1)[CH:6]=O.[CH:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.Cl.[OH2:20]>>[O:11]=[C:9]1[CH2:10][C:3](=[O:2])[CH:4]=[C:5](/[CH:6]=[C:13]2/[C:18](=[O:20])[CH2:17][CH2:16][CH2:15][CH2:14]/2)[CH2:8]1

Participants

5

Reactant 4

HCID 241BenzeneHCID 313Hydrochloric AcidHCID 962WaterHCID 817473,5-Dimethoxybenzaldehyde

Product 1

HCID 118366098HCID 118366098, compoundYield 74%

Procedure

10.79 g (0.11 mol) of cyclohexanone and 10.4 g (0.12 mol) of morpholine were added to 20 mL benzene, refluxed azeotropically after a trap was equipped, when no water was generated, benzene and morpholine were evaporated under reduced pressure to give enamine. 6.54 g (0.043 mol) of enamine and 5.40 g (0.033 mol) of 3,5-dimethoxybenzaldehyde were added to 20 mL benzene, refluxed azeotropically after a trap was equipped until no water was generated in a total of 8 h, after cooling to room temperature, 6 mol/L hydrochloric acid was added slowly with stirring, and stirred at room temperature for 2 h, the benzene layer was separated, the aqueous layer was extracted with benzene layer, benzene layers were combined and dried over anhydrous sodium sulfate, after evaporating the solvent under reduced pressure and recrystallizing with petroleum ether and ethanol, E-2-(3,5-dioxobenzylidene)cyclohexanone was obtained as yellow needles, yield: 74%, mp 55.0˜56.6. 1H-NMR: δ: 7.41 (s, 1H, ═CH), 6.53 (d, 2H, J=2.0 Hz, ArH), 6.45 (t, 1H, J=2.0 Hz, ArH), 3.80 (s, 6H, OCH3), 2.84 (dt, 2H, J=1.9, 6.5 Hz, CH2), 2.54 (t, 2H, J=6.6 Hz, CH2), 1.90 (m, 2H, CH2), 1.78 (m, 2H, CH2).

Workup

  1. temperaturerefluxed azeotropically after a trap
  2. customwas generated in a total of 8 h
  3. stirringstirred at room temperature for 2 h
  4. customthe benzene layer was separated
  5. extractionthe aqueous layer was extracted with benzene layer, benzene layers
  6. dry with materialdried over anhydrous sodium sulfate
  7. customafter evaporating the solvent under reduced pressure
  8. customrecrystallizing with petroleum ether and ethanol

Sources & evidence

ORD record
ord-c576607315f34501bdece22bb16ffe33
Source dataset
uspto-grants-2016_08
Patent number
US09409845B2

Reaction notes

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