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

HRID 279912

反応式

HRID 279912 の反応式
[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]

参加物

5

反応物 3

HCID 5564TriclosanHCID 8471TriethylamineHCID 778283-Methylglutaric anhydride

生成物 1

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

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9c22268e69f445f58f3de5e07ed5e4a6
出典データセット
uspto-grants-1986_05
特許番号
US04587262

関連ノート

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