Methyl vinyl ketone → HCID 54012949, compound

HRID 1196246Notes

Reaction equation

HRID 1196246 reaction equation
[CH3:1][C:2](=[O:5])[CH:3]=[CH2:4].[Cl:6][C:7]1[CH:8]=[C:9]([CH:13]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=2)[CH:14]=O)[CH:10]=[CH:11][CH:12]=1.[OH-].[K+]>C(OCC)C.C(O)C.C(OCC)(=O)C.O>[Cl:6][C:7]1[CH:8]=[C:9]([C:13]2([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=3)[CH2:14][CH2:1][C:2](=[O:5])[CH:3]=[CH:4]2)[CH:10]=[CH:11][CH:12]=1

Participants

8

Reactant 3

HCID 6570Methyl vinyl ketoneHCID 14797Potassium HydroxideHCID 54374521HCID 54374521, compound

Product 1

HCID 54012949HCID 54012949, compound

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Butenone (11.3 cc) is added to a solution of bis(3-chlorophenyl)acetaldehyde (36.9 g) in ethyl ether (200 cc), and then, after cooling to 0° C., a solution of potassium hydroxide (3.1 g) in ethanol (20 cc) is added dropwise. The reaction mixture is stirred for 2 h at 0° C. and then for 16 hours at 25° C. and diluted with ethyl acetate (100 cc) and water (200 cc). The aqueous phase is washed with ethyl acetate (100 cc). The combined organic phases are washed with saturated sodium chloride solution (3×100 cc), dried over magnesium sulphate and concentrated under reduced pressure (2.7 kPa). The residue is chromatographed on a column of silica gel (particle size 0.04-0.063 mm, diameter 7 cm, height 42 cm), eluting under a nitrogen pressure of 0.5 bar with a mixture of cyclohexane and ethyl acetate (90:10). 4,4-Bis(3-chlorophenyl)cyclohexenone (27.7 g) is obtained in the form of a yellow oil.

Workup

  1. waitfor 16 hours at 25° C.
  2. washThe aqueous phase is washed with ethyl acetate (100 cc)
  3. washThe combined organic phases are washed with saturated sodium chloride solution (3×100 cc)
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated under reduced pressure (2.7 kPa)
  6. customThe residue is chromatographed on a column of silica gel (particle size 0.04-0.063 mm, diameter 7 cm, height 42 cm)
  7. washeluting under a nitrogen pressure of 0.5 bar
  8. additionwith a mixture of cyclohexane and ethyl acetate (90:10)

Sources & evidence

ORD record
ord-b1f12e598fe4454a9a855e8b0696a373
Source dataset
uspto-grants-1992_05
Patent number
US05112988

Reaction notes

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