2,4,6-Trichlorophenol → 2-Bromohexadecanoic acid phenylester

HRID 1456915Notes

Reaction equation

HRID 1456915 reaction equation
[Br:1][CH:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[C:3]([OH:5])=[O:4].Cl[C:21]1[CH:26]=[C:25](Cl)[CH:24]=[C:23](Cl)[C:22]=1O.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)(Cl)Cl.ClCCl.CO>[C:21]1([O:4][C:3](=[O:5])[CH:2]([Br:1])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 69142,4,6-TrichlorophenolHCID 10868DicyclohexylcarbodiimideHCID 821452-Bromohexadecanoic acid

Product 1

HCID 544857572-Bromohexadecanoic acid phenylester

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 21226129Dichloromethane methanolSolvent

Procedure

2-Bromohexadecanoic acid (1 g) was dissolved in dry chloroform (20 ml). After addition of 2,4,6 trichlorophenol (0.558 g), the reaction mixture was placed in an ice bath. Dicyclohexylcarbodiimide (0.736 g) dissolved in dry chloroform (2 ml) was added to the solution. After stirring the solution for 15 minutes in an ice bath, the temperature was adjusted to 20° C. Formation of the product was ascertained by thin layer chromatography on silicic-acid plates with dichloromethane/methanol (10:0.1 v/v) mixture as solvent. The solution was stirred for 24 h at 20° C. and the precipitated urea removed by filtration. The filtrate was washed twice with sodium bicarbonate (0.05M) solution and water. The crude reaction product was purified by liquid chromatography on silica gel using the same solvent system as eluent.

Workup

  1. customthe reaction mixture was placed in an ice bath
  2. additionwas added to the solution
  3. customwas adjusted to 20° C
  4. stirringThe solution was stirred for 24 h at 20° C.
  5. customthe precipitated urea removed by filtration
  6. washThe filtrate was washed twice with sodium bicarbonate (0.05M) solution and water
  7. customThe crude reaction product
  8. customwas purified by liquid chromatography on silica gel using the same solvent system as eluent

Sources & evidence

ORD record
ord-82cfa230b6744f9ab0a2d6d915640586
Source dataset
uspto-grants-1998_12
Patent number
US05846951

Reaction notes

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