4'-Hydroxyacetophenone → HCID 19100382, compound

HRID 2254499Notes

Reaction equation

HRID 2254499 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.[F:11][CH:12]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH2:13]OS(C1C=CC(C)=CC=1)(=O)=O.[OH-].[K+]>C(O)CCC>[F:11][CH:12]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH2:13][O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 74694'-HydroxyacetophenoneHCID 14797Potassium HydroxideHCID 14297706HCID 14297706, compound

Product 1

HCID 19100382HCID 19100382, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent2×

Procedure

Then, 6.3 g of p-hydroxyacetophenone and 12.7 g of 2-fluorooctyl-p-toluenesulfonate were dissolved in 35 ml of butanol. To the solution, a solution of 3.1 g of potassium hydroxide in 40 ml of butanol was added dropwise, followed by heat-refluxing for 6 hours. After the reaction, the reaction mixture was poured into 200 ml of ice water and extracted with isopropyl ether. The organic layer was washed with water and dried with anhydrous magnesium sulfate, followed by distilling-off of the solvent to precipitate a crystal. The crystal was purified by silica gel column chromatography to obtain 4.7 g of p-(2-fluorooctyloxy)acetophenone.

Workup

  1. temperatureby heat-refluxing for 6 hours
  2. customAfter the reaction
  3. extractionextracted with isopropyl ether
  4. washThe organic layer was washed with water
  5. dry with materialdried with anhydrous magnesium sulfate
  6. customto precipitate a crystal
  7. customThe crystal was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ef072e3f6f2b4e858eae04f57f2650dd
Source dataset
uspto-grants-1993_08
Patent number
US05236619

Reaction notes

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