Hydrochloric Acid → HCID 13370661, compound

HRID 2412969Notes

Reaction equation

HRID 2412969 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=O)[CH:10]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[CH2:11][CH2:12][C:13](=[O:15])[CH3:14])=[CH:5][CH:4]=1.[OH-].[K+].Cl.C1(=O)CCCC=C1>C(O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=3)[CH2:11][CH2:12][C:13](=[O:15])[CH:14]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 135942-Cyclohexen-1-oneHCID 14797Potassium HydroxideHCID 13370660HCID 13370660, compound

Product 1

HCID 13370661HCID 13370661, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 212.0 g. of 1,2-bis(4-methoxyphenyl)-1,5-hexanedione and 650 ml. of 2N potassium hydroxide in three liters of 2B ethanol was heated to reflux for two hours. The solution was cooled and 110 ml. of concentrated hydrochloric acid were added. The solution was then concentrated in vacuo. One liter of water and 1.5 liters of ethyl acetate were added to the residue. The layers were separated. The aqueous layer was extracted three times each with 800 ml. of ethyl acetate. The combined organic layers were washed four times with water, dried over sodium sulfate, filtered and evaporated in vacuo to provide 195.6 g. of the desired cyclohexenone intermediate as an oil.

Workup

  1. temperatureto reflux for two hours
  2. temperatureThe solution was cooled
  3. concentrationThe solution was then concentrated in vacuo
  4. additionOne liter of water and 1.5 liters of ethyl acetate were added to the residue
  5. customThe layers were separated
  6. extractionThe aqueous layer was extracted three times each with 800 ml
  7. washThe combined organic layers were washed four times with water
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. customevaporated in vacuo
  11. customto provide 195.6 g

Sources & evidence

ORD record
ord-84d0ec72dff7442db7c0433f02b834c4
Source dataset
uspto-grants-1985_01
Patent number
US04495202

Reaction notes

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