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

HRID 279911

反応式

HRID 279911 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][C:19]1([CH3:27])[CH2:25][CH2:24][C:23](=[O:26])[O:22][C:20]1=[O:21]>C(N(CC)CC)C>[C:23]([CH2:24][CH2:25][C:19]([CH3:27])([CH3:18])[C:20]([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:21])([OH:26])=[O:22]

参加物

4

反応物 2

HCID 5564TriclosanHCID 76247Dihydro-3,3-dimethyl-2H-pyran-2,6(3H)-dione

生成物 1

HCID 233229055-Chloro-2-(2,4-dichlorophenoxy)phenyl 4-carboxy-2,2-dimethylbutyrate

試薬・触媒・溶媒 1

HCID 8471Triethylamine溶媒2 回

反応条件

温度
80 °C

実験手順

A mixture of triclosan (29.0 g.), triethylamine (15 ml.) and 2,2-dimethylglutaric anhydride (20 g.) was heated at 80° C. for 5 hours. A further quantity (2.0 g.) of anhydride and triethylamine (1 ml.) were added and heating continued for 24 hours. The mixture was cooled to ambient temperature, washed with 2M hydrochloric acid (100 ml.), then with water (3×80 ml.) and dried (MgSO4). The solution obtained was evaporated. The brown residual oil was dissolved in hot cyclohexane. The solution on cooling gave white crystals which were recrystallised from cyclohexane/petrol 60-80 to give 5-chloro-2-(2,4-dichlorophenoxy)phenyl 4-carboxy-2,2-dimethylbutyrate (C') (12.7 g.), m.p. 125°-128° C.

後処理

  1. temperatureheating
  2. temperatureThe mixture was cooled to ambient temperature
  3. washwashed with 2M hydrochloric acid (100 ml.)
  4. dry with materialwith water (3×80 ml.) and dried (MgSO4)
  5. customThe solution obtained
  6. customwas evaporated
  7. dissolutionThe brown residual oil was dissolved in hot cyclohexane
  8. temperatureThe solution on cooling
  9. customgave white crystals which
  10. customwere recrystallised from cyclohexane/petrol 60-80

出典と根拠

ORDレコード
ord-d097fe9abe56492db156157af1bcf77c
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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