6-m-Methoxyphenylhex-1-en-3-one → 2-Cetyl-2-(6-m-methoxyphenyl-3-oxohexyl)-1,3-cyclopentanedione

HRID 1077149Notes

Reaction equation

HRID 1077149 reaction equation
[CH2:1]([CH:17]1[C:21](=[O:22])[CH2:20][CH2:19][C:18]1=[O:23])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[CH3:24][O:25][C:26]1[CH:27]=[C:28]([CH2:32][CH2:33][CH2:34][C:35](=[O:38])[CH:36]=[CH2:37])[CH:29]=[CH:30][CH:31]=1>[OH-].[K+]>[CH2:1]([C:17]1([CH2:37][CH2:36][C:35](=[O:38])[CH2:34][CH2:33][CH2:32][C:28]2[CH:29]=[CH:30][CH:31]=[C:26]([O:25][CH3:24])[CH:27]=2)[C:18](=[O:23])[CH2:19][CH2:20][C:21]1=[O:22])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

4

Reactant 2

HCID 107982386-m-Methoxyphenylhex-1-en-3-oneHCID 136224282-Cetylcyclopentane-1,3-dione

Product 1

HCID 214855912-Cetyl-2-(6-m-methoxyphenyl-3-oxohexyl)-1,3-cyclopentanedioneYield 73.7%

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Procedure

Reflux a mixture of 2-cetylcyclopentane-1,3-dione (10.1 g), 6-m-methoxyphenylhex-1-en-3-one (6.0 g) and 0.02% methanolic potassium hydroxide solution (120 cc) for 26 hours and then cool. Dissolve the residue obtained after removal of solvent under reduced pressure in a mixture of benzene (50 cc) and ether (50 cc), and wash the solution in turn with sodium carbonate solution, 10% aqueous sulfuric acid and water. Remove the solvent by evaporation under reduced pressure to obtain as residue crude 2-cetyl-2-(6-m-methoxyphenyl-3-oxohexyl)-1,3-cyclopentanedione (11.4 g).

Workup

  1. temperatureReflux
  2. temperaturecool
  3. dissolutionDissolve the residue
  4. customobtained
  5. customafter removal of solvent under reduced pressure
  6. additionin a mixture of benzene (50 cc) and ether (50 cc)
  7. washwash the solution in turn with sodium carbonate solution, 10% aqueous sulfuric acid and water
  8. customRemove the solvent
  9. customby evaporation under reduced pressure

Sources & evidence

ORD record
ord-c583580bbd4d44a6a037a2af8282a163
Source dataset
uspto-grants-1976_05
Patent number
US03959322

Reaction notes

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