Methyl Ethyl Ketone → HCID 20061646, compound

HRID 1085200Notes

Reaction equation

HRID 1085200 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:16])[CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:4][CH:3]=1.C([C:19]1[C:20](Br)=[C:21]([C:26]([O-:28])=[O:27])[C:22]([CH3:25])=[CH:23][CH:24]=1)C.C(=O)([O-])[O-].[K+].[K+].[CH3:36][C:37](=O)CC>[I-].[K+]>[CH2:36]([O:28][C:26]([C:21]1[CH:20]=[CH:19][CH:24]=[CH:23][C:22]=1[CH2:25][O:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([CH3:16])[CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:6][CH:7]=1)=[O:27])[CH3:37]

Participants

6

Reactant 4

HCID 6569Methyl Ethyl KetoneHCID 11430Potassium CarbonateHCID 13603942HCID 13603942, compoundHCID 86744725HCID 86744725, compound

Product 1

HCID 20061646HCID 20061646, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 4875Potassium IodideCatalyst

Procedure

A mixture of 12 g of ethyl 4-(4-hydroxyphenyl)pentanoate, 16.05 g of ethyl -bromo-o-toluate, 0.5 g of pulverized potassium iodide and 36.49 g of potassium carbonate in 300 ml of 2-butanone was heated under reflux overnight. The salts were collected and washed with ether. The filtrate was evaporated and the residue was partitioned between water and ether. The organic layer was separated, washed with 10% sodium hydroxide solution and water, dried over anhydrous sodium sulfate, filtered and evaporated. Chromatography on a Waters Associates Prep LC-System 500 (two silica gel columns; elution with dichloromethane) gave 12.15 g (59%) of product, as an oil.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux overnight
  3. customThe salts were collected
  4. washwashed with ether
  5. customThe filtrate was evaporated
  6. customthe residue was partitioned between water and ether
  7. customThe organic layer was separated
  8. washwashed with 10% sodium hydroxide solution and water
  9. dry with materialdried over anhydrous sodium sulfate
  10. filtrationfiltered
  11. customevaporated
  12. washChromatography on a Waters Associates Prep LC-System 500 (two silica gel columns; elution with dichloromethane)

Sources & evidence

ORD record
ord-f8e57f3758e6478c8f9d776b3eb65cb9
Source dataset
uspto-grants-1991_04
Patent number
US05008285

Reaction notes

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