Reaction #1061889

Reaction equation

4-octyloxybenzoic acid

2,4,5-trichlorophenol

N,N'-dicyclohexylcarbodiimide

→

2,4,5-trichlorophenyl 4-octyloxybenzoate

Yield 32.0%

Solvents

diethyl ether

Conditions

Workup

1. 1
   OtherThe precipitate was removed by filtration
2. 2
   Concentrationthe filtrate was concentrated in vacuo
3. 3
   workup.DISSOLUTIONThe residue was dissolved in petroleum ether
4. 4
   FiltrationThe resulting crystals (15.2 g) were filtered
5. 5
   workup.DISSOLUTIONdissolved in warm n-hexane (150 ml)
6. 6
   workup.WAITAfter standing overnight at room temperature
7. 7
   Otherthe resulting crystals were removed by filtration
8. 8
   ConcentrationThe filtrate was concentrated to an oil which
9. 9
   Otherwas purified by a column chromatography (silica gel)
10. 10
    workup.ADDITIONa mixture of ethyl acetate and n-hexane

Procedure

To a solution of 4-octyloxybenzoic acid (13.8 g) in diethyl ether (552 ml) were added 2,4,5-trichlorophenol (10.87 g) and N,N'-dicyclohexylcarbodiimide (11.37 g). The solution was stirred under a nitrogen atmosphere for 18 hours at room temperature. The precipitate was removed by filtration, and the filtrate was concentrated in vacuo. The residue was dissolved in petroleum ether and was allowed to stand on ice-water. The resulting crystals (15.2 g) were filtered and dissolved in warm n-hexane (150 ml). After standing overnight at room temperature, the resulting crystals were removed by filtration. The filtrate was concentrated to an oil which was purified by a column chromatography (silica gel) using a mixture of ethyl acetate and n-hexane to give 2,4,5-trichlorophenyl 4-octyloxybenzoate (7.58 g) (m.p. 53° C., Anal: Calcd. for C21H23O3Cl3 :Cl24.75, Found: Cl 24.05).

Source