Acetone → 3-(4-(4-propylcyclohexyl)cyclohexyl)-2E-propenal

HRID 2399604Notes

Reaction equation

HRID 2399604 reaction equation
[CH2:1]([CH:4]1[CH2:9][CH2:8][CH:7]([CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[CH2:6][CH2:5]1)[CH2:2][CH3:3].[OH2:16].[CH3:17][C:18]([CH3:20])=O>Cl>[CH2:17]([CH:13]1[CH2:14][CH2:15][CH:10]([CH:7]2[CH2:8][CH2:9][CH:4](/[CH:1]=[CH:2]/[CH:3]=[O:16])[CH2:5][CH2:6]2)[CH2:11][CH2:12]1)[CH2:18][CH3:20]

Participants

5

Reactant 3

HCID 180AcetoneHCID 962WaterHCID 178840974-(4-Propylcyclohexyl)cyclohexane

Product 1

HCID 120204373-(4-(4-propylcyclohexyl)cyclohexyl)-2E-propenal

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

The resulting cyclohexane derivative was dissolved in a mixed solvent of acetone (80 ml) with 2N hydrochloric acid (8 ml) , followed by heating the solution under reflux for 4 hours, cooling the reaction mixture down to room temperature after completion of the stirring, adding water, extracting with ether (50 ml), drying the organic layer over anhydrous magnesium sulfate, and concentrating under reduced pressure to obtain 3-(4-(4-propylcyclohexyl)cyclohexyl)-2E-propenal (3.1 g, 12 mmols). This product was used in the subsequent reaction without any purification.

Workup

  1. temperatureby heating the solution
  2. temperatureunder reflux for 4 hours
  3. extractionextracting with ether (50 ml)
  4. dry with materialdrying the organic layer over anhydrous magnesium sulfate
  5. concentrationconcentrating under reduced pressure

Sources & evidence

ORD record
ord-9c18e53ab95c47c4a8d53fdbc341e28f
Source dataset
uspto-grants-1995_09
Patent number
US05449810

Reaction notes

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