Potassium Hydroxide → HCID 86684776, compound

HRID 330780Notes

Reaction equation

HRID 330780 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([NH:11]C(=O)C)=[CH:7][C:6]=1[O:15][CH2:16][CH2:17][O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:2][CH2:3][CH3:4].[OH-].[K+]>C(O)C.O.C(Cl)Cl>[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[CH:7][C:6]=1[O:15][CH2:16][CH2:17][O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 2

HCID 14797Potassium HydroxideHCID 86684777HCID 86684777, compound

Product 1

HCID 86684776HCID 86684776, compoundYield 80%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

N-(4-Butyl-3-(2-phenoxyethoxy)phenyl)acetamide (132 g, 0.41 mol) was dissolved in ethanol (897 mL) and water (104 mL). KOH (312 g, 5.57 mol) was added at 0° C. and the solution was allowed to reflux for 18 hrs. Upon completion the reaction was cooled to room temperature and diluted with 2 L of water and 2 L of DCM. The organic layer was washed with water (×2) and dried over sodium sulfate. The crude compound was purified further via flash chromatography with hexane:ethyl acetate (1:1) to obtain the title compound in 80% yield (92 g) as a pink solid.

Workup

  1. temperatureto reflux for 18 hrs
  2. washThe organic layer was washed with water (×2)
  3. dry with materialdried over sodium sulfate
  4. customThe crude compound was purified further via flash chromatography with hexane:ethyl acetate (1:1)

Sources & evidence

ORD record
ord-921698ba76d749c299f86a2e8fcd58df
Source dataset
uspto-grants-2014_11
Patent number
US08877752B2

Reaction notes

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