Hydrochloric Acid → 4-Cyclohexyl-3-methyl-4-oxo-3-phenylbutanal

HRID 479340Notes

Reaction equation

HRID 479340 reaction equation
C([O:3][CH:4](OCC)[CH2:5][C:6]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([C:8]([CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1)=[O:9])[CH3:7])C.Cl>CC(C)=O>[C:16]1([C:6]([C:8]([CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)=[O:9])([CH3:7])[CH2:5][CH:4]=[O:3])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 110240791-Cyclohexyl-4,4-diethoxy-2-methyl-2-phenylbutan-1-one

Product 1

HCID 117801924-Cyclohexyl-3-methyl-4-oxo-3-phenylbutanalYield 99.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1,1-Diethoxy-3-phenyl-3-cyclohexanecarbonyl-butane (74.4 g, 224 mmol) was dissolved in acetone (800 mL) followed by addition of 3.0 N HCl (800 mL). The reaction mixture was stirred for one hour at room temperature. It was then concentrated under vacuum to less than ½ its original volume and then extracted with methylene chloride (800 mL). The organic extract was then washed with brine (300 mL), dried over anhydrous magnesium sulfate, suction filtered and concentrated under vacuum to provide crude 3-phenyl-3-cyclohexanecarbonyl-butan-1-al (57.8 g). Alternatively, the dried and filtered methylene chloride solution can be used directly in the next step without concentration.

Workup

  1. concentrationIt was then concentrated under vacuum to less than ½ its original volume
  2. extractionextracted with methylene chloride (800 mL)
  3. extractionThe organic extract
  4. washwas then washed with brine (300 mL)
  5. dry with materialdried over anhydrous magnesium sulfate, suction
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-90b1f5fcd09a41a49e2a6404402a9fec
Source dataset
uspto-grants-2003_11
Patent number
US06645967B2

Reaction notes

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