4'-Hydroxyacetophenone → HCID 2724918, compound

HRID 920522Notes

Reaction equation

HRID 920522 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.[OH-].[K+].Br[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]>CS(C)=O>[CH2:14]([O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Participants

5

Reactant 3

HCID 74694'-HydroxyacetophenoneHCID 81401-BromooctaneHCID 14797Potassium Hydroxide

Product 1

HCID 2724918HCID 2724918, compoundYield 94.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 4′-hydroxyacetophenone (25.0 g; 183.6 mmol) in DMSO (300. mL) was added KOH (11.3 g; 201.9 mmol.) and the reaction mixture was stirred for 1 hour at RT. After 1 hour the reaction mixture was cooled (0° C.) and 1-bromooctane (34.9 mL; 201.9 mmol) was added. The ice bath was removed and the reaction mixture was stirred overnight at RT. The reaction mixture was extracted with EtOAc/5% aqueous NaHCO3 solution. The organic layer was dried with Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography (SiO2, Et2O:hexanes 1:3) to afford 1-(4-octyloxy-phenyl)-ethanone (43.08 g)

Workup

  1. additionwas added
  2. customThe ice bath was removed
  3. stirringthe reaction mixture was stirred overnight at RT
  4. extractionThe reaction mixture was extracted with EtOAc/5% aqueous NaHCO3 solution
  5. dry with materialThe organic layer was dried with Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography (SiO2, Et2O:hexanes 1:3)

Sources & evidence

ORD record
ord-1f5f95b1fc2548cca382cabd3b2bd559
Source dataset
uspto-grants-2016_03
Patent number
US09273017B2

Reaction notes

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