4'-Hydroxypropiophenone → HCID 86085445, compound

HRID 1669247

Reaction equation

HRID 1669247 reaction equation
[OH-].[Na+].[OH:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:13])[CH2:11][CH3:12])=[CH:6][CH:5]=1.Cl[CH2:15][C:16]1[C:17]([CH3:25])=[C:18]([CH3:24])[CH:19]=[C:20]([CH3:23])[C:21]=1[CH3:22]>CCO.O>[CH3:22][C:21]1[C:20]([CH3:23])=[CH:19][C:18]([CH3:24])=[C:17]([CH3:25])[C:16]=1[CH2:15][O:3][C:4]1[CH:5]=[CH:6][C:7]([C:10](=[O:13])[CH2:11][CH3:12])=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 62714'-HydroxypropiophenoneHCID 14798Sodium HydroxideHCID 819393-(Chloromethyl)-1,2,4,5-tetramethylbenzene

Product 1

HCID 86085445HCID 86085445, compoundYield 67.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

NaOH (1.6 g, 40 mmol) is added to the solution of 1-(4-hydroxy-phenyl)-propan-1-one (3.0 g, 20 mmol) in EtOH (50 mL) and water (30 mL), followed by the addition of 3-Chloromethyl-1,2,4,5-tetramethyl-benzene (5.5 g, 30 mol). The resulting mixture is heated to turn into clear solution and stirred at room temperature overnight. The reaction is quenched by 1N HCl and extracted with ethyl acetate (3×100 mL). The combined organic layers are washed with water, brine, dried (MgSO4), concentrated and chromatographed to afford the titled compound as a white solid (4.0 g).

Workup

  1. temperatureThe resulting mixture is heated
  2. customThe reaction is quenched by 1N HCl
  3. extractionextracted with ethyl acetate (3×100 mL)
  4. washThe combined organic layers are washed with water, brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customchromatographed

Sources & evidence

ORD record
ord-c3a58e85ffe24f79bd6fe328aa87a9f6
Source dataset
uspto-grants-2011_08
Patent number
US07989457B2

Linked notes

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