Acetophenone → Ccris 2231

HRID 36738

Reaction equation

HRID 36738 reaction equation
[OH-].[Na+].[CH:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][CH:5]=1.[C:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(=O)[CH3:14]>CCO.O>[CH3:11][O:10][C:7]1[CH:8]=[CH:9][C:4]([C:3](=[O:12])[CH:14]=[CH:13][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 7410AcetophenoneHCID 14798Sodium HydroxideHCID 312444-Methoxybenzaldehyde

Product 1

HCID 92853Ccris 2231Yield 56%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Step A Add 10% aqueous NaOH (38 mL) to a solution of p-anisaldehyde (25 mL, 0.206 mol) and acetophenone (23.97 mL, 0.206 mol) in EtOH (500 mL). Stir the mixture at room temperature over night. Dilute the mixture with water and extract with ether. Combine the ethereal extracts, wash with water and brine, dry over Na2SO4 and concentrate to a solid. Recrystallize the solid from ether/hexanes to provide 27.51 g (56%) of 4'-methoxychalcone, mp 72°-74° C.

Workup

  1. extractionextract with ether
  2. washwash with water and brine
  3. dry with materialdry over Na2SO4
  4. concentrationconcentrate to a solid
  5. customRecrystallize the solid from ether/hexanes

Sources & evidence

ORD record
ord-8a78853258fc48d2bcf415d810e7317d
Source dataset
uspto-grants-1995_05
Patent number
US05416118

Linked notes

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