Hydrochloric Acid → 5-(3,4-Dimethoxyphenyl)-3-ethoxy-2-cyclohexen-1-one

HRID 1108755Notes

Reaction equation

HRID 1108755 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]2[CH2:16][C:15](=[O:17])[CH2:14][C:13](=[O:18])[CH2:12]2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].Cl.[CH2:20](O)[CH3:21]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]2[CH2:16][C:15](=[O:17])[CH:14]=[C:13]([O:18][CH2:20][CH3:21])[CH2:12]2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 8541355-(3,4-Dimethoxyphenyl)cyclohexane-1,3-dione

Product 1

HCID 187841445-(3,4-Dimethoxyphenyl)-3-ethoxy-2-cyclohexen-1-oneYield 29.1%

Procedure

5-(3,4-Dimethoxyphenyl)cyclohexan-1,3-dione (31.8 g) was suspended in ethanol (500 ml), and concentrated hydrochloric acid (20 ml) was added prior to reflux for 3 hours. After the reaction solvent was concentrated under reduced pressure, it was dissolved in chloroform and washed with saturated sodium bicarbonate water. After drying with anhydrous magnesium sulfate, the solvent was concentrated under reduced pressure producing crude crystals which were then washed with diethyl ether to give 10.3 g of 5-(3,4-dimethoxyphenyl)-3-ethoxy-2-cyclohexen-1-one (29.1%).

Workup

  1. temperatureto reflux for 3 hours
  2. concentrationAfter the reaction solvent was concentrated under reduced pressure, it
  3. dissolutionwas dissolved in chloroform
  4. washwashed with saturated sodium bicarbonate water
  5. dry with materialAfter drying with anhydrous magnesium sulfate
  6. concentrationthe solvent was concentrated under reduced pressure
  7. customproducing crude crystals which
  8. washwere then washed with diethyl ether

Sources & evidence

ORD record
ord-1559a75d965c414f82d9ec0768d3e888
Source dataset
uspto-grants-2000_05
Patent number
US06069176

Reaction notes

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