1,3-Cyclohexadiene → HCID 14267379, compound

HRID 2059723Notes

Reaction equation

HRID 2059723 reaction equation
[C:1]1(=[O:8])[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]1.[Cl-].[Al+3].[Cl-].[Cl-].[CH:13]1[CH2:18][CH2:17][CH:16]=[CH:15][CH:14]=1>C1(C)C=CC=CC=1>[CH:18]12[CH2:17][CH2:16][CH:15]([CH:7]3[C:1](=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH:6]31)[CH:14]=[CH:13]2

Participants

5

Reactant 3

HCID 116051,3-CyclohexadieneHCID 707232-Cyclohepten-1-oneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 14267379HCID 14267379, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a solution of (Z)-cyclohept-2-enone (1.4 g, 10 mmol) in dry toluene was added aluminum chloride (0.67 g, 5 mmol) and the resulting mixture was stirred at room temperature for 40 minutes. A solution of cyclohexadiene (9.62 g, 120 mmol) in toluene was added dropwise, and the mixture was stirred overnight at 40° C. The reaction mixture was filtered through diatomaceous earth and then partition in ethyl acetate/water. The organic layer was washed with sodium bicarbonate solution, dried (magnesium sulfate), filtered, evaporated under vacuum and purified by chromatography on silica gel eluting with 5-10% ether/hexane to provide the title compound: MS (DCl/NH3) m/z 191 (M+H)+, 208 (M+NH4)+.

Workup

  1. stirringthe mixture was stirred overnight at 40° C
  2. filtrationThe reaction mixture was filtered through diatomaceous earth
  3. custompartition in ethyl acetate/water
  4. washThe organic layer was washed with sodium bicarbonate solution
  5. dry with materialdried (magnesium sulfate)
  6. filtrationfiltered
  7. customevaporated under vacuum
  8. custompurified by chromatography on silica gel eluting with 5-10% ether/hexane

Sources & evidence

ORD record
ord-35dcce9058cc4b16b8ea7c65763d0ae9
Source dataset
uspto-grants-2012_10
Patent number
US08278311B2

Reaction notes

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