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

HRID 279911

반응식

HRID 279911 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][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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8471Triethylamine용매2회

반응 조건

온도
80 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-d097fe9abe56492db156157af1bcf77c
출처 데이터셋
uspto-grants-1986_05
특허 번호
US04587262

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