Chloroacetic Acid → 2-(4-Methylthiophenyl)ethoxyacetic acid

HRID 1905971노트

반응식

HRID 1905971 반응식
[CH3:1][S:2][C:3]1[CH:11]=[CH:10][C:6]([CH2:7][CH2:8][OH:9])=[CH:5][CH:4]=1.[H-].[Na+].Cl[CH2:15][C:16]([OH:18])=[O:17].O>CS(C)=O>[CH3:1][S:2][C:3]1[CH:11]=[CH:10][C:6]([CH2:7][CH2:8][O:9][CH2:15][C:16]([OH:18])=[O:17])=[CH:5][CH:4]=1

참가 물질

6

반응물 4

HCID 300Chloroacetic AcidHCID 962WaterHCID 24758Sodium hydrideHCID 27600862-(4-Methylsulfanylphenyl)ethanol

생성물 1

HCID 132089272-(4-Methylthiophenyl)ethoxyacetic acid수율 46.1%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
60 °C

실험 절차

6.27 g of 4-methylthiophenethyl alcohol in 100 ml of dimethyl sulfoxide were treated with 3.58 g of a 50% sodium hydride dispersion in mineral oil and the mixture was stirred at 60° C. for 10 minutes. 3.53 g of chloroacetic acid were added and the heating was continued at 80° C. for 3 hours while stirring. The mixture was cooled, poured into water and washed with ethyl acetate. The aqueous phase was acidified to pH 1 with concentrated hydrochloric acid and extracted with ethyl acetate. The organic phase was separated, washed well with water, dried over sodium sulfate, filtered and evaporated to dryness. The residue was recrystallized from toluene/hexane to give 3.89 g (46%) of 2-(4-methylthiophenyl)ethoxyacetic acid of melting 58°-60° C.

후처리

  1. waitthe heating was continued at 80° C. for 3 hours
  2. stirringwhile stirring
  3. temperatureThe mixture was cooled
  4. washwashed with ethyl acetate
  5. extractionextracted with ethyl acetate
  6. customThe organic phase was separated
  7. washwashed well with water
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. customevaporated to dryness
  11. customThe residue was recrystallized from toluene/hexane

출처 및 근거

ORD 기록
ord-7546e7c372a341e78972a311d7b7679b
출처 데이터셋
uspto-grants-1987_03
특허 번호
US04649160

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