Cyclohexyl methyl ketone → HCID 54220593, compound

HRID 2293873Notes

Reaction equation

HRID 2293873 reaction equation
[O-]CC.[Na+].[CH:5]1([C:11](=[O:13])[CH3:12])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.[F:14][C:15]1[CH:22]=[CH:21][C:18]([CH:19]=O)=[CH:17][CH:16]=1>C(O)C.CCOCC>[CH:5]1([C:11](=[O:13])[CH:12]=[CH:19][C:18]2[CH:21]=[CH:22][C:15]([F:14])=[CH:16][CH:17]=2)[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1

Participants

6

Reactant 3

HCID 13207Cyclohexyl methyl ketoneHCID 680234-FluorobenzaldehydeHCID 2723922Sodium ethoxide

Product 1

HCID 54220593HCID 54220593, compoundYield 69.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A sodium ethoxide solution (21% by weight in ethanol, 6.805 gm, 21 mmol) was added to a mixture of 1-cyclohexyl-1-ethanone (18.749g, 140 mmol, from Aldrich) and 4-fluorobenzaldehyde (17.37g, 140 mmol, from Aldrich) in ethanol (100 ml), stirring under argon. The solution was allowed to stir 1.5 hours. The reaction mixture was then concentrated to afford an orange oil. The oil was dissolved in ether, washed with saturated NH4Cl and brine, then dried over Na2SO4, filtered and concentrated to an orange oil. The oil was purified by distillation (bp=143° C. at 1.3 mm Hg). The resultant yellowish oil slowly solidified to afford the title compound as hard yellow crystals (22.640 gm, 65%).

Workup

  1. stirringto stir 1.5 hours
  2. concentrationThe reaction mixture was then concentrated
  3. customto afford an orange oil
  4. washwashed with saturated NH4Cl and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated to an orange oil
  8. distillationThe oil was purified by distillation (bp=143° C. at 1.3 mm Hg)

Sources & evidence

ORD record
ord-0651e0ef23f8405bb0101ae226b31660
Source dataset
uspto-grants-1997_11
Patent number
US05686433

Reaction notes

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