Triclosan → 5-Chloro-2-(2,4-dichlorophenoxy)phenyl 4-carboxy-3-methylbutyrate

HRID 279912

Reaction equation

HRID 279912 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.[CH3:18][CH:19]1[CH2:25][C:24](=[O:26])[O:23][C:21](=[O:22])[CH2:20]1.C(N(CC)CC)C>CCOCC>[C:21]([CH2:20][CH:19]([CH3:18])[CH2:25][C:24]([O:8][C:4]1[CH:5]=[C:6]([Cl:7])[CH:1]=[CH:2][C:3]=1[O:9][C:10]1[CH:11]=[CH:12][C:13]([Cl:17])=[CH:14][C:15]=1[Cl:16])=[O:26])([OH:23])=[O:22]

Participants

5

Reactant 3

HCID 5564TriclosanHCID 8471TriethylamineHCID 778283-Methylglutaric anhydride

Product 1

HCID 233228965-Chloro-2-(2,4-dichlorophenoxy)phenyl 4-carboxy-3-methylbutyrateYield 23%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of triclosan (22.3 g.), 3-methylglutaric anhydride (15.0 g.) and triethylamine (15 ml.) in ether (250 ml.) was stirred for 20 hours, and then washed first with 2M hydrochloric acid (50 ml.) and then with water (3×150 ml.). The ether phase was dried (MgSO4) and evaporated. A portion (20 g.) of the residual oil was purified by chromatography on silica gel using methylene chloride as eluant to give (D) as a colourless oil (7.4 g.) ; NMR (CDCl3): 0.8-1.3 (3H,d, CH3), 2.1-2.8 (5H,m,CH2CO+CH3CH), 6.7-7.6 (6H, m, aromatic H), 11.25 (1H,s, CO2H)ppm.

Workup

  1. washwashed first with 2M hydrochloric acid (50 ml.)
  2. dry with materialThe ether phase was dried (MgSO4)
  3. customevaporated
  4. customA portion (20 g.) of the residual oil was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-9c22268e69f445f58f3de5e07ed5e4a6
Source dataset
uspto-grants-1986_05
Patent number
US04587262

Linked notes

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