Triclosan → Benzyloxy-acetic acid 5-chloro-2-(2,4-dichloro-phenoxy)-phenyl ester

HRID 1949181

Reaction equation

HRID 1949181 reaction equation
[CH:1]1[C:6]([Cl:7])=[CH:5][C:4]([OH:8])=[C:3]([O:9][C:10]2[CH:11]=[CH:12][C:13]([Cl:17])=[CH:14][C:15]=2[Cl:16])[CH:2]=1.C(N(CC)CC)C.[CH2:25]([O:32][CH2:33][C:34](Cl)=[O:35])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CC(C)=O>[Cl:7][C:6]1[CH:1]=[CH:2][C:3]([O:9][C:10]2[CH:11]=[CH:12][C:13]([Cl:17])=[CH:14][C:15]=2[Cl:16])=[C:4]([O:8][C:34](=[O:35])[CH2:33][O:32][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:5]=1

Participants

5

Reactant 3

HCID 5564TriclosanHCID 8471TriethylamineHCID 177085Benzyloxyacetyl chloride

Product 1

HCID 57667396Benzyloxy-acetic acid 5-chloro-2-(2,4-dichloro-phenoxy)-phenyl ester

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mixture of triclosan (7.53 grams, 26 mmol) and triethylamine (8.2 grams, 81 mmol) in acetone (50 mL) at 0° C. was added benzyloxy acetyl chloride (10 grams, 54.2 mmol) drop wise. The reaction mixture was stirred at room temperature for 18 hours. Solids were filtered off and poured onto cold water (100 mL). Crude 4 was extracted into chloroform, washed with 5% sodium bicarbonate solution (2×50 mL), and water (2×50 mL). The chloroform layer was dried over sodium sulphate and distilled off to get crude 4.

Workup

  1. filtrationSolids were filtered off
  2. additionpoured onto cold water (100 mL)
  3. extractionCrude 4 was extracted into chloroform
  4. washwashed with 5% sodium bicarbonate solution (2×50 mL), and water (2×50 mL)
  5. dry with materialThe chloroform layer was dried over sodium sulphate
  6. distillationdistilled off
  7. customto get crude 4

Sources & evidence

ORD record
ord-99aa6b9310a04be393bfc254b99f5a32
Source dataset
uspto-grants-2013_03
Patent number
US08399696B2

Linked notes

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