Water → Ethyl 4-(4-fluorophenoxy)benzoate

HRID 1741003Notes

Reaction equation

HRID 1741003 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.F[C:10]1[CH:20]=[CH:19][C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:12][CH:11]=1.O.CCCCCC.C(OCC)(=O)C>CS(C)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:10]2[CH:20]=[CH:19][C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 97324-FluorophenolHCID 67976Benzoic acid, 4-fluoro-, ethyl esterHCID 21226206Ethyl acetate hexane

Product 1

HCID 21834365Ethyl 4-(4-fluorophenoxy)benzoateYield 60.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

p-Fluorophenol (1.66 g, 14.81 mmol) and ethyl p-fluorobenzoate (2.50 g, 14.87 mmol) were dissolved in 30 ml of dry DMSO and treated with 1.7 g of KF/alumina and 0.39 g of crown ether (18-C-6). The reaction mixture was heated at 100° C. for sixty hours, cooled and poured into 100 ml of water. The mixture was extracted twice with 250 ml of diethyl ether. The extracts were washed with water and then brine, combined, dried over MgSO4 and concentrated. Medium-pressure liquid chromatography over silica using 30:1 hexane/ethyl acetate afforded 2.32 g (60% yield) of the subtitle compound.

Workup

  1. temperaturecooled
  2. extractionThe mixture was extracted twice with 250 ml of diethyl ether
  3. washThe extracts were washed with water
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-686effb04cc848b888d5dc447bbb04fe
Source dataset
uspto-grants-1999_10
Patent number
US05972972

Reaction notes

Loading…