Triclosan → 5-Chloro-2-(2,4-dichlorophenoxy)phenyl prop-2-enoate

HRID 991379Notes

Reaction equation

HRID 991379 reaction equation
[CH:1]1[C:6]([Cl:7])=[CH:5][C:4]([OH:8])=[C:3]([O:9][C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=2[Cl:17])[CH:2]=1.C(N(CC)CC)C.[C:25](Cl)(=[O:28])[CH:26]=[CH2:27]>O1CCCC1>[CH2:27]=[CH:26][C:25]([O:8][C:4]1[CH:5]=[C:6]([Cl:7])[CH:1]=[CH:2][C:3]=1[O:9][C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=1[Cl:17])=[O:28]

Participants

5

Reactant 3

HCID 5564TriclosanHCID 8471TriethylamineHCID 13140Acryloyl chloride2×

Product 1

HCID 673466385-Chloro-2-(2,4-dichlorophenoxy)phenyl prop-2-enoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

Irgasan® DP300 5-chloro-2-(2,4-dichlorophenol)(triclosan), 23.5 g (0.081 mol) was dissolved in 300 ml of dry tetrahydrofuran in a 1-l jacketed kettle with agitator, addition funnel and reflux condenser. Then 10.6 ml of triethylamine was added to the solution with agitation. To the resulting solution was added dropwise 6.68 (0.0738 mol) g of acryloyl chloride. The reaction temperature was maintained at 20° C. with a circulating cooling bath. After the addition of acryloyl chloride was completed, the agitation and temperature conditions were maintained for 5 hours. Then the reaction product was kept overnight at room temperature, filtered to remove solid triethylamine hydrochloride and the filtrate rotovapped at room temperature under 100-110 mm Hg to concentrate the product. The remaining solution was dissolved in 100 ml heptane and washed with 5% Na2CO3 solution in Dl water until basic; then with Dl water until neutral. The heptane solution of the product was dried with MgSO4 in a refrigerator overnight, and filtered. The filtrate contained 25.3% triclosan acrylate as determined by bromination. FTIR spectrum confirmed the presence of the unsaturated ester of a phenol (1753 cm−1).

Workup

  1. temperaturereflux condenser
  2. temperaturea circulating cooling bath
  3. temperaturethe agitation and temperature conditions were maintained for 5 hours
  4. filtrationfiltered
  5. customto remove solid triethylamine hydrochloride
  6. customrotovapped at room temperature under 100-110 mm Hg
  7. concentrationto concentrate the product
  8. dissolutionThe remaining solution was dissolved in 100 ml heptane
  9. washwashed with 5% Na2CO3 solution in Dl water until basic
  10. dry with materialThe heptane solution of the product was dried with MgSO4 in a refrigerator overnight
  11. filtrationfiltered

Sources & evidence

ORD record
ord-541733ca58234a7d962701877abd65d5
Source dataset
uspto-grants-2002_10
Patent number
US06464961B2

Reaction notes

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