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

HRID 279912

반응식

HRID 279912 반응식
[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]

참가 물질

5

반응물 3

HCID 5564TriclosanHCID 8471TriethylamineHCID 778283-Methylglutaric anhydride

생성물 1

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

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9c22268e69f445f58f3de5e07ed5e4a6
출처 데이터셋
uspto-grants-1986_05
특허 번호
US04587262

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