Hydrochloric Acid → 2-Cyclopentyl-3-methoxycyclohex-3-en-1-one

HRID 1609800Notes

Reaction equation

HRID 1609800 reaction equation
[CH:1]1([CH:6]2[C:11]([O:12][CH3:13])=[CH:10][CH2:9][CH:8]=[C:7]2[O:14]C)[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl>CO>[CH:1]1([CH:6]2[C:11]([O:12][CH3:13])=[CH:10][CH2:9][CH2:8][C:7]2=[O:14])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 222600866-Cyclopentyl-1,5-dimethoxy-cyclohexa-1,4-diene

Product 1

HCID 222600872-Cyclopentyl-3-methoxycyclohex-3-en-1-oneYield 94.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-cyclopentyl-2,5-dihydro-1,3dimethoxybenzene (5 g, 27 mmol) in methanol (50 mL) was added 2.5% hydrochloric acid (10 mL) dropwise at 0° C. The reaction mixture was stirred for 45 minutes and diluted with 30 mL of ice-cold water. The product was extracted with ether (3×100 mL). The combined organic extract was washed with brine and dried (Na2SO4). Removal of the solvent in vacuo yielded the title compound as light yellow oil (4.3 g, 94.7%).

Workup

  1. extractionThe product was extracted with ether (3×100 mL)
  2. extractionThe combined organic extract
  3. washwas washed with brine
  4. dry with materialdried (Na2SO4)
  5. customRemoval of the solvent in vacuo

Sources & evidence

ORD record
ord-e93b9678d5f746a29526b21670272f71
Source dataset
uspto-grants-2006_01
Patent number
US06982260B1

Reaction notes

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