Benzaldehyde → 2,6-Bis(benzylidene)cyclohexanone

HRID 1415292Notes

Reaction equation

HRID 1415292 reaction equation
[C:1]1(=[O:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:8](=O)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.Cl>C(O)C>[C:9]1([CH:8]=[C:2]2[CH2:3][CH2:4][CH2:5][C:6](=[CH:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:1]2=[O:7])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 313Hydrochloric AcidHCID 7967Cyclohexanone

Product 1

HCID 953362,6-Bis(benzylidene)cyclohexanoneYield 63%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 32.0 g (0.33 mole) of cyclohexanone, 70.0 g (0.66 mole) of benzaldehyde, 200 ml of ethanol and 20 ml of concentrated HCl is heated and then refluxed for one hour. Crystallization from the deep red solution occurs and after cooling the crystallized 2,6-bis(phenylmethylene)cyclohexanone is filtered and washed with cold ethanol and dried yielding 72.0 g; m.p. 114°-116° . This material is recrystallized from 120 ml of DMF (dimethylformamide) yielding 56.0 g (63%) of yellow 2,6-bis(phenylmethylene)cyclohexanone; m.p. 114°-116° .

Workup

  1. temperaturerefluxed for one hour
  2. customCrystallization from the deep red solution
  3. temperatureafter cooling the crystallized 2,6-bis(phenylmethylene)cyclohexanone
  4. filtrationis filtered
  5. washwashed with cold ethanol
  6. customdried
  7. customyielding 72.0 g
  8. customThis material is recrystallized from 120 ml of DMF (dimethylformamide)

Sources & evidence

ORD record
ord-cfaeb23051fe4f16836d97fe470c245d
Source dataset
uspto-grants-1977_01
Patent number
US04004007

Reaction notes

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