Hydrochloric Acid → 2-(2,6-Dimethyl-4-prop-1-ynylphenyl)cyclopentane-1,3-dione

HRID 514192Notes

Reaction equation

HRID 514192 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]#[C:9][CH3:10])[CH:5]=[C:4]([CH3:11])[C:3]=1[C:12]1[C:13](=[O:19])[CH2:14][CH2:15][C:16]=1[O:17]C.Cl.O.C(OCC)(=O)C>CC(C)=O>[CH3:1][C:2]1[CH:7]=[C:6]([C:8]#[C:9][CH3:10])[CH:5]=[C:4]([CH3:11])[C:3]=1[CH:12]1[C:13](=[O:19])[CH2:14][CH2:15][C:16]1=[O:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8857Ethyl AcetateHCID 896009282-(2,6-Dimethyl-4-prop-1-ynylphenyl)-3-methoxycyclopent-2-enone

Product 1

HCID 896013122-(2,6-Dimethyl-4-prop-1-ynylphenyl)cyclopentane-1,3-dione

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2-(2,6-dimethyl-4-prop-1-ynylphenyl)-3-methoxycyclopent-2-enone (0.193 g, 0.76 mmol) in acetone (2.0 ml) is added 2M hydrochloric acid (2.0 ml). The mixture is heated at 60°C. under microwave irradiation for 20 minutes, then distilled water and ethyl acetate are added and the phases separated. The aqueous phase is extracted with ethyl acetate (×3), and combined organic fractions are washed with brine, dried over magnesium sulfate, filtered and the filtrate concentrated in vacuo. The crude product is purified by flash column chromatography (ethyl acetate and isohexane as eluant) to afford 2-(2,6-dimethyl-4-prop-1-ynylphenyl)cyclopentane-1,3-dione.

Workup

  1. customthe phases separated
  2. extractionThe aqueous phase is extracted with ethyl acetate (×3)
  3. washare washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated in vacuo
  7. customThe crude product is purified by flash column chromatography (ethyl acetate and isohexane as eluant)

Sources & evidence

ORD record
ord-dc29a29065d741cda675e5f524dcc1f5
Source dataset
uspto-grants-2015_08
Patent number
US09107415B2

Reaction notes

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