Dichloromethane → 2-Chloro-5,5-diphenylcyclohexa-1,3-dienecarbaldehyde

HRID 1243852Notes

Reaction equation

HRID 1243852 reaction equation
P(Cl)(Cl)(Cl)=O.CN(C=[C:10]1[C:15](=[O:16])[CH:14]=[CH:13][C:12]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:11]1)C.Cl[CH2:30][Cl:31]>>[Cl:31][C:30]1[CH:10]=[CH:11][C:12]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:13][C:14]=1[CH:15]=[O:16]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 24813Phosphorus oxychlorideHCID 695944896-Dimethylaminomethylene-4,4-diphenylcyclohex-2-enone

Product 1

HCID 219286962-Chloro-5,5-diphenylcyclohexa-1,3-dienecarbaldehyde

Conditions

Temperature
20 °C

Procedure

0.193 cm3 of phosphorus oxychloride is added to a solution of 0.607 g of 6-dimethylaminomethylene-4,4-diphenylcyclohex-2-enone in 15 cm3 of dichloromethane. The mixture is heated to the reflux temperature and refluxing is maintained for about 3 hours. After cooling to a temperature in the region of 20° C., the solution is concentrated to dryness under reduced pressure (13 kPa). The residue is dissolved in 20 cm3 of tetrahydrofuran and 20 cm3 of water are added in a single portion. The mixture is refluxed for about 24 hours. After cooling to a temperature in the region of 20° C., the mixture is concentrated to dryness under reduced pressure (13 kPa). The residue is taken up in 10 cm3 of ethyl acetate. The solution is washed three times with 30 cm3 of water and then dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (13 kPa). 0.6 g of 2-chloro-5,5-diphenylcyclohexa-1,3-dienecarbaldehyde is thus obtained in the form of an orange-coloured resin, which is used without further modification in subsequent syntheses and the characteristics of which are as follows:

Workup

  1. temperatureThe mixture is heated to the reflux temperature
  2. temperaturerefluxing
  3. temperatureis maintained for about 3 hours
  4. concentrationthe solution is concentrated to dryness under reduced pressure (13 kPa)
  5. dissolutionThe residue is dissolved in 20 cm3 of tetrahydrofuran
  6. addition20 cm3 of water are added in a single portion
  7. temperatureThe mixture is refluxed for about 24 hours
  8. temperatureAfter cooling to a temperature in the region of 20° C.
  9. concentrationthe mixture is concentrated to dryness under reduced pressure (13 kPa)
  10. washThe solution is washed three times with 30 cm3 of water
  11. dry with materialdried over magnesium sulphate
  12. filtrationfiltered
  13. concentrationconcentrated to dryness under reduced pressure (13 kPa)

Sources & evidence

ORD record
ord-c287981146a64624bb9b4e2832becbb0
Source dataset
uspto-grants-2006_10
Patent number
US07119115B2

Reaction notes

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