Benzaldehyde → HCID 134806, compound

HRID 1578511Notes

Reaction equation

HRID 1578511 reaction equation
[C:1]1(=[O:9])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:10](=O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[OH-].[K+].CO>C(O)(C)(C)C>[CH:10](=[C:2]1[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8](=[CH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:1]1=[O:9])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 887MethanolHCID 10403CyclooctanoneHCID 14797Potassium Hydroxide

Product 1

HCID 134806HCID 134806, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

An alternative procedure for preparing 2,8-dibenzylcyclooctanones involves the corresponding 2,8-dibenzylidenecyclooctanones as the intermediates. Thus, a mixture comprising 12.5 grams of cyclooctanone, 27 grams of benzaldehyde, 15 grams of potassium hydroxide and 300 milliliters of methanol is stirred at reflux temperatures for 4 hours. To the hot, stirred mixture are slowly added 400 milliliters of t-butyl alcohol with simultaneous removal of the methanol by distillation. The mixture is then cooled, water is added and the product is extracted with ether. The crude product obtained from the ether extract is chromatographed on activated alumina to give 2,8-dibenzylidenecyclooctanone. This intermediate is hydrogenated at 60 p.s.i.g. in ethanol using 5 percent palladium on carbon. Fractional crystallization of the hydrogenation product from methanol affords the isomeric 2,8-dibenzylcyclooctanones, m.p. 75°-77° C. and 66°-68° C.

Workup

  1. temperatureat reflux temperatures for 4 hours
  2. stirringTo the hot, stirred mixture
  3. customwith simultaneous removal of the methanol
  4. distillationby distillation
  5. temperatureThe mixture is then cooled
  6. additionwater is added
  7. extractionthe product is extracted with ether
  8. customThe crude product obtained from the ether
  9. extractionextract
  10. customis chromatographed on activated alumina

Sources & evidence

ORD record
ord-fed9ac6d19b5408d8df4df33941dbab0
Source dataset
uspto-grants-1976_02
Patent number
US03937710

Reaction notes

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