Methyl vinyl ketone → HCID 54188104, compound

HRID 1029952Notes

Reaction equation

HRID 1029952 reaction equation
[CH3:1][C:2](=[O:5])[CH:3]=[CH2:4].[C:6]1([CH3:22])[CH:11]=[CH:10][CH:9]=[C:8]([CH:12]([C:15]2[CH:16]=[C:17]([CH3:21])[CH:18]=[CH:19][CH:20]=2)[CH:13]=O)[CH:7]=1.[OH-].[K+]>C(OCC)C.C(O)C.C(OCC)(=O)C.O>[C:17]1([CH3:21])[CH:18]=[CH:19][CH:20]=[C:15]([C:12]2([C:8]3[CH:7]=[C:6]([CH3:22])[CH:11]=[CH:10][CH:9]=3)[CH2:13][CH2:1][C:2](=[O:5])[CH:3]=[CH:4]2)[CH:16]=1

Participants

8

Reactant 3

HCID 6570Methyl vinyl ketoneHCID 14797Potassium HydroxideHCID 54162423HCID 54162423, compound

Product 1

HCID 54188104HCID 54188104, compound

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Butenone (7.23 cc) is added to a solution of bis-(3-tolyl)acetaldehyde (20.4 g) in ethyl ether (110 cc) and then, after cooling to 0° C., a solution of potassium hydroxide (2 g) in ethanol (12.7 cc) is added dropwise. The reaction mixture is stirred for 2 hours at 0° C. and then for 16 hours at 25° C. and diluted with ethyl acetate (200 cc) and water (200 cc). The aqueous phase is washed with ethyl acetate (2×250 cc). The combined organic phases are washed with water (2×250 cc) and then with saturated sodium chloride solution (250 cc), dried over magnesium sulphate and concentrated under reduced pressure (2.7 kPa). The residue is chromatographed on silica gel (particle size 0.04-0.063 mm, column 5.4 cm in diameter and 40 cm high), eluting under a nitrogen pressure of 0.5 bar with a mixture of cyclohexane and ethyl acetate (85/15 by volume). 4,4 -bis-(3-Tolyl)-cyclohexenone (16.7 g) is obtained in the form of yellow oil.

Workup

  1. waitfor 16 hours at 25° C.
  2. washThe aqueous phase is washed with ethyl acetate (2×250 cc)
  3. washThe combined organic phases are washed with water (2×250 cc)
  4. dry with materialwith saturated sodium chloride solution (250 cc), dried over magnesium sulphate
  5. concentrationconcentrated under reduced pressure (2.7 kPa)
  6. customThe residue is chromatographed on silica gel (particle size 0.04-0.063 mm, column 5.4 cm in diameter and 40 cm high)
  7. washeluting under a nitrogen pressure of 0.5 bar
  8. additionwith a mixture of cyclohexane and ethyl acetate (85/15 by volume)

Sources & evidence

ORD record
ord-57514e1469d5425b8af83bdd14d64a0b
Source dataset
uspto-grants-1992_04
Patent number
US05102667

Reaction notes

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