Hydrochloric Acid → 3-(4-Octylphenyl)cyclohex-2-enone

HRID 1511868Notes

Reaction equation

HRID 1511868 reaction equation
[Mg].Br[C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[CH:5][CH:4]=1.C([O:19][C:20]1[CH2:25][CH2:24][CH2:23][C:22](=O)[CH:21]=1)C.Cl>C1COCC1.CCOCC>[CH2:9]([C:6]1[CH:7]=[CH:8][C:3]([C:22]2[CH2:23][CH2:24][CH2:25][C:20](=[O:19])[CH:21]=2)=[CH:4][CH:5]=1)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 792163-Ethoxycyclohex-2-ene-1-oneHCID 142854p-BromophenyloctaneHCID 5462224Magnesium

Product 1

HCID 575547273-(4-Octylphenyl)cyclohex-2-enoneYield 66%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of magnesium (1.477 g, 60.8 mmol) in THF (56 mL) was added 1-bromo-4-octylbenzene (15.00 g, 55.7 mmol). After stirring for about 6 h the reaction mixture was added with filtering to a solution of 3-ethoxycyclohex-2-enone (7.10 g, 50.6 mmol) in THF (28.0 mL) at 0° C. Following the addition the reaction mixture was allowed to warm to room temperature. After 1 h 1N HCl was added until a pH of 1 was obtained. The reaction mixture was diluted with Et2O and the organic layer was separated, washed with NaHCO3, and brine, dried with (Na2SO4, filtered and concentrated in vacuo. The crude product was purified by chromatography on silica gel (EtOAc/Hep) to provide 3-(4-octylphenyl)cyclohex-2-enone (9.5 g, 33.4 mmol, 65.9% yield) as a colorless oil.

Workup

  1. additionwas added
  2. additionthe addition the reaction mixture
  3. customwas obtained
  4. customthe organic layer was separated
  5. washwashed with NaHCO3, and brine
  6. dry with materialdried with (Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude product was purified by chromatography on silica gel (EtOAc/Hep)

Sources & evidence

ORD record
ord-164906bfca424a4f855335f25e1e9759
Source dataset
uspto-grants-2012_07
Patent number
US08217027B2

Reaction notes

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