Potassium Iodide → Ethyl [4-(4-phenylbutoxy)phenoxy]acetate

HRID 2422211Notes

Reaction equation

HRID 2422211 reaction equation
[OH:1][C:2]1[CH:14]=[CH:13][C:5]([O:6][CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:4][CH:3]=1.[C:15]1([CH2:21][CH2:22][CH2:23][CH2:24]Br)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C)C=O>[C:15]1([CH2:21][CH2:22][CH2:23][CH2:24][O:1][C:2]2[CH:3]=[CH:4][C:5]([O:6][CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:13][CH:14]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 2596681-Bromo-4-phenylbutaneHCID 13187337Ethyl 2-(4-hydroxyphenoxy)acetate

Product 1

HCID 85970854Ethyl [4-(4-phenylbutoxy)phenoxy]acetateYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of ethyl (4-hydroxyphenoxy)acetate (0.49 g, 2.5 mmol), 4-phenylbutyl bromide (0.59 g, 2.8 mmol), potassium carbonate (0.69 g, 5.0 mmol) and potassium iodide (30 mg, 0.50 mmol) in N,N-dimethylformamide (5 mL) was stirred at room temperature for 30 min., and further at 50° C. for 3 hrs. The solvent was evaporated under reduced pressure, and the residue was partitioned between ethyl acetate and saturated brine. The organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=4:1) to give the title compound (0.62 g, yield 76%). oil.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was partitioned between ethyl acetate and saturated brine
  3. concentrationThe organic layer was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=4:1)

Sources & evidence

ORD record
ord-dcd3b6e83f6b4dcba5fa9e348e0fe62c
Source dataset
uspto-grants-2011_06
Patent number
US07960369B2

Reaction notes

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