2,4,5-Trichlorophenol → 2,4,5-Trichlorophenyl 4-n-Octyloxybenzoate

HRID 1492893Notes

Reaction equation

HRID 1492893 reaction equation
[CH2:1]([O:9][C:10]1[CH:18]=[CH:17][C:13]([C:14]([OH:16])=[O:15])=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[Cl:19][C:20]1[CH:25]=[C:24]([Cl:26])[C:23]([Cl:27])=[CH:22][C:21]=1O.C1(N=C=NC2CCCCC2)CCCCC1>C(OCC)C>[CH2:1]([O:9][C:10]1[CH:11]=[CH:12][C:13]([C:14]([O:16][C:21]2[CH:22]=[C:23]([Cl:27])[C:24]([Cl:26])=[CH:25][C:20]=2[Cl:19])=[O:15])=[CH:17][CH:18]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 72712,4,5-TrichlorophenolHCID 10868DicyclohexylcarbodiimideHCID 172314-(Octyloxy)benzoic acid

Product 1

HCID 6162082,4,5-Trichlorophenyl 4-n-OctyloxybenzoateYield 32%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

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 crystal was removed by filtration. The filtrate was concentrated to an oil which was purified by a column chromatography over silica gel using a mixture of ethyl acetate and n-hexane to give 2,4,5-trichlorophenyl 4-octyloxybenzoate (7.58 g) (MP 53° C., Anal Calcd. for C21H23O3Cl3 : Cl 24.75, Found: Cl 24.05).

Workup

  1. customThe precipitate was removed by filtration
  2. concentrationthe filtrate was concentrated in vacuo
  3. dissolutionThe residue was dissolved in petroleum ether
  4. filtrationThe resulting crystals (15.2 g) were filtered
  5. dissolutiondissolved in warm n-hexane (150 ml)
  6. waitAfter standing overnight at room temperature
  7. customthe resulting crystal was removed by filtration
  8. concentrationThe filtrate was concentrated to an oil which
  9. customwas purified by a column chromatography over silica gel using
  10. additiona mixture of ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-ed2def42c30b4090a9998f3005158991
Source dataset
uspto-grants-1994_12
Patent number
US05376634

Reaction notes

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