Hydrochloric Acid → 4-[2-(4-(4-Methyl-3-pentenyl)-3-cyclohexenyl)ethyl]-1-(4-pentyl-3-cyclohexenyl)methoxybenzene

HRID 2227104Notes

Reaction equation

HRID 2227104 reaction equation
[CH3:1][C:2]([CH3:21])=[CH:3][CH2:4][CH2:5][C:6]1[CH2:11][CH2:10][CH:9]([CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17](O)=[CH:16][CH:15]=2)[CH2:8][CH:7]=1.S([C:26]1[CH:32]=[CH:31][C:29]([CH3:30])=[CH:28][CH:27]=1)([O-])(=O)=O.[C:33](=[O:36])([O-])[O-].[Cs+].[Cs+].Cl>CN(C)C=O>[CH3:1][C:2]([CH3:21])=[CH:3][CH2:4][CH2:5][C:6]1[CH2:11][CH2:10][CH:9]([CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:36][CH2:33][CH:26]3[CH2:32][CH2:31][C:29]([CH2:30][CH2:1][CH2:2][CH2:3][CH3:4])=[CH:28][CH2:27]3)=[CH:16][CH:15]=2)[CH2:8][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 85570p-ToluenesulfonateHCID 184718234-[2-(4-(4-Methyl-3-pentenyl)-3-cyclohexenyl)ethyl]phenol

Product 1

HCID 184718074-[2-(4-(4-Methyl-3-pentenyl)-3-cyclohexenyl)ethyl]-1-(4-pentyl-3-cyclohexenyl)methoxybenzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a round-bottom flask equipped with a stirbar is added phenol 2G (R=4-Methyl-3-pentenyl) (5 g), tosylate 1H (R=n-pentyl) (5.95 g), cesium carbonate (7.45 g), and anhydrous dimethylforrnamide (50 mL). The reaction mixture is stirred overnight. It is then poured into 50 mL dilute HCl, and extracted with 1:1 hexanes:ethyl acetate. The combined organic layers are washed with brine and dried over potassium carbonate, and the solution is concentrated in vacuo. Filtration through silica gel using 10% ethyl acetate in hexanes gives the pure product.

Workup

  1. customTo a round-bottom flask equipped with a stirbar
  2. extractionextracted with 1:1 hexanes
  3. washThe combined organic layers are washed with brine
  4. dry with materialdried over potassium carbonate
  5. concentrationthe solution is concentrated in vacuo
  6. filtrationFiltration through silica gel using 10% ethyl acetate in hexanes
  7. customgives the pure product

Sources & evidence

ORD record
ord-0fbff6eecf894940af7bdd948d3e542c
Source dataset
uspto-grants-2002_07
Patent number
US06413448B1

Reaction notes

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