Hydrochloric Acid → 2-Isopropyl-3-methoxy-cyclohex-3-enone

HRID 1609792Notes

Reaction equation

HRID 1609792 reaction equation
[CH:1]([CH:4]1[C:9]([O:10][CH3:11])=[CH:8][CH2:7][CH:6]=[C:5]1[O:12]C)([CH3:3])[CH3:2].Cl>CO>[CH:1]([CH:4]1[C:9]([O:10][CH3:11])=[CH:8][CH2:7][CH2:6][C:5]1=[O:12])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 112983266-Isopropyl-1,5-dimethoxy-cyclohexa-1,4-diene

Product 1

HCID 222601702-Isopropyl-3-methoxy-cyclohex-3-enoneYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 6-isopropyl-1,5dimethoxy-cyclohexa-1,4-diene (7 g) in methanol (50 mL) was added 2.5% hydrochloric acid (10 mL) drop wise at 0° C. The reaction mixture was stirred for 45 minutes, then diluted with ice-cold water (30 mL). The product was extracted with ether (3×70 mL). The combined organic extracts were washed with brine and dried over anhydrous sodium sulfate. Removal of the solvent in vacuo yielded the title compound as a light yellow oil (6 g, 93%).

Workup

  1. extractionThe product was extracted with ether (3×70 mL)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customRemoval of the solvent in vacuo

Sources & evidence

ORD record
ord-5ec5f94d3bf943ea9ec627ac9b948ce4
Source dataset
uspto-grants-2006_01
Patent number
US06982260B1

Reaction notes

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