Cyclohexanone → HCID 13747869, compound

HRID 247500Notes

Reaction equation

HRID 247500 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH2:10][CH3:11])[CH:6]=[C:5]([C:12]([CH3:20])([CH3:19])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH:4]=1.C([Li])CCC.[CH2:26]1[CH2:31][CH2:30][CH2:29][CH2:28][C:27]1=[O:32].[Cl-].[NH4+]>CCOCC.CCCCCC>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:12]([CH3:19])([CH3:20])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH:6]=[C:7]([O:9][CH2:10][CH3:11])[C:8]=1[CH:31]1[CH2:30][CH2:29][CH2:28][C:27](=[O:32])[CH2:26]1

Participants

7

Reactant 4

HCID 7967CyclohexanoneHCID 25517Ammonium ChlorideHCID 13747868HCID 13747868, compoundHCID 178418339Butyllithium

Product 1

HCID 13747869HCID 13747869, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

1-Methoxy-3-(1,1-dimethylheptyl)-5-ethoxybenzene (IIa) (1500 mg, 5.4 mmol) was dissolved in dry ether (25 ml) and the solution was cooled to 0° C. The reaction was placed under nitrogen and butyl lithium (5.94 mmol, 3.6 ml of a solution in hexane) was injected into the reaction. The reaction mixture was brought to room temperature, and was stirred for 4 hrs. Cuprous bromide (360 mg, 2.5 mmol) was added in one portion. The reaction mixture turned dark and became homogeneous. After stirring for 5 min, 2-cyclohexanone (240 mg, 2.5 mmol) was injected into the solution, and the reaction mixture was stirred for 15 min at 0°. Ether (50 ml) and a saturated ammonium chloride solution (150 ml) were added. The organic layer was washed with brine, dried and evaporated to dryness. The oil obtained was purified by medium pressure liquid chromatography (230-400 mesh ASTM, silica gel 60" for column chromatography; elution with petroleum ether, b.p. 60°-80°) to yield the title compound, IIIa (66%).

Workup

  1. customwas brought to room temperature
  2. stirringAfter stirring for 5 min
  3. stirringthe reaction mixture was stirred for 15 min at 0°
  4. washThe organic layer was washed with brine
  5. customdried
  6. customevaporated to dryness
  7. customThe oil obtained
  8. customwas purified by medium pressure liquid chromatography (230-400 mesh ASTM, silica gel 60" for column chromatography; elution with petroleum ether, b.p. 60°-80°)

Sources & evidence

ORD record
ord-a87210f746f6461daa3e868bb4e601a6
Source dataset
uspto-grants-1987_11
Patent number
US04707559

Reaction notes

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