2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 4,4-Diphenyl-2-formyl-2-cyclohexen-1-one

HRID 1196264Notes

Reaction equation

HRID 1196264 reaction equation
[C:1]1([C:7]2([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:12][CH2:11][C:10](=[O:13])[CH:9]([CH:14]=[O:15])[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>O1CCOCC1>[C:1]1([C:7]2([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:12][CH2:11][C:10](=[O:13])[C:9]([CH:14]=[O:15])=[CH:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 54244847HCID 54244847, compound

Product 1

HCID 537947534,4-Diphenyl-2-formyl-2-cyclohexen-1-oneYield 27.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 4,4-diphenyl-2-formylcyclohexanone (44.5 g) and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (38 g) in dioxane (650 cc) is stirred for 30 minutes at 25° C. and then cooled to 0° C.; the solid is removed by filtration and the filtrate is concentrated to dryness under reduced pressure (2.7 kPa). The residue is chromatographed on a column of silica gel (0.2-0.06 mm, diameter 6 cm, height 63 cm), eluting with a mixture of cyclohexane and ethyl acetate (80:20 by volume) and collecting 50-cc fractions. Fractions 7 to 12 are combined and concentrated to dryness under reduced pressure (2.7 kPa). The crystalline residue is stirred vigorously with isopropyl ether (200 cc) and the crystals obtained are drained, washed with isopropyl ether (2×50 cc) and dried. 4,4-Diphenyl-2-formyl-2-cyclohexen-1-one (12 g), m.p. 126° C., is obtained.

Workup

  1. customthe solid is removed by filtration
  2. concentrationthe filtrate is concentrated to dryness under reduced pressure (2.7 kPa)
  3. customThe residue is chromatographed on a column of silica gel (0.2-0.06 mm, diameter 6 cm, height 63 cm)
  4. washeluting with a mixture of cyclohexane and ethyl acetate (80:20 by volume)
  5. customcollecting 50-cc fractions
  6. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  7. customthe crystals obtained
  8. washwashed with isopropyl ether (2×50 cc)
  9. customdried

Sources & evidence

ORD record
ord-f2d4818838cf492a912d31a4e29e5f05
Source dataset
uspto-grants-1992_05
Patent number
US05112988

Reaction notes

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