3-(Dimethylamino)phenol → HCID 15728465, compound

HRID 1645923Notes

Reaction equation

HRID 1645923 reaction equation
[CH3:1][N:2]([CH3:10])[C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.C(=O)([O-])[O-].[K+].[K+].[CH:17]1[CH:22]=[C:21]([Cl:23])[CH:20]=[C:19]([C:24]([CH2:26]Br)=[O:25])[CH:18]=1>CC(C)=O>[Cl:23][C:21]1[CH:20]=[C:19]([C:24](=[O:25])[CH2:26][O:9][C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([N:2]([CH3:10])[CH3:1])[CH:4]=2)[CH:18]=[CH:17][CH:22]=1

Participants

5

Reactant 3

HCID 74213-(Dimethylamino)phenolHCID 11430Potassium CarbonateHCID 387382-Bromo-3'-chloroacetophenone

Product 1

HCID 15728465HCID 15728465, compoundYield 47.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A slurry of 3.0 g of 3-dimethylaminophenol, 6.05 g of milled potassium carbonate and 75 ml of acetone was stirred at room temperature under nitrogen for 30 minutes and then a solution of 7.66 g of α-bromo-3-chloroacetophenone in 75 ml of acetone was added dropwise. The slurry was stirred at room temperature for 72 hours. Filtration and evaporation gave a residue which was purified by high performance liquid chromatography (7:1 hexane-ethyl acetate). The resulting solid was recrystallized from ethyl acetate-hexane to give 3.0 g of 1-(3-chlorophenyl)-2-[3-(dimethylamino)phenoxy]ethanone, m.p. 101°-103° C.

Workup

  1. filtrationFiltration and evaporation
  2. customgave a residue which
  3. customwas purified by high performance liquid chromatography (7:1 hexane-ethyl acetate)
  4. customThe resulting solid was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-66d58e30f1ea4f22beee4c447809e250
Source dataset
uspto-grants-1993_01
Patent number
US05177111

Reaction notes

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