p-Toluenesulfonic acid → 2-Carboxy-3-methyl-5,6-dihydro-1,4-dithiin

HRID 1415307

반응식

HRID 1415307 반응식
[CH:1]([SH:4])(S)[CH3:2].Cl[CH:6]([C:12]([CH3:14])=O)[C:7]([O:9]CC)=[O:8].C1(C)C=CC([S:21](O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH3:14][C:12]1[S:4][CH2:1][CH2:2][S:21][C:6]=1[C:7]([OH:9])=[O:8]

참가 물질

5

반응물 3

HCID 6101p-Toluenesulfonic acidHCID 11858Ethyl 2-chloroacetoacetateHCID 336451,1-Ethanedithiol

생성물 1

HCID 6005022-Carboxy-3-methyl-5,6-dihydro-1,4-dithiin

시약·촉매·용매 1

HCID 241Benzene용매

실험 절차

Ethanedithiol (94 g) and ethyl alpha-chloroacetoacetate (164.5 g) were dissolved in benzene (500 g), a trace of p-toluenesulfonic acid added, and the whole solution refluxed under a Dean-Stark trap for one hour, when 16 cc of water had collected. The solution was cooled, washed with ice-cold dilute caustic soda and the benzene removed in vacuo. Ethanolic caustic soda (80 g in the minimum amount of ethanol) was added and the solution refluxed for 30 minutes, then cooled, diluted with water (one volume), and made acid with dilute HCl. The thick white precipitate was filtered, washed with water and recrystallized from ethanol to give 5,6-dihydro-3-methyl-1,4-dithiin-2-carboxylic acid as long white needles, m.p. 173°-175°, yield 92 g (52%).

후처리

  1. temperaturethe whole solution refluxed under a Dean-Stark trap for one hour
  2. customwhen 16 cc of water had collected
  3. temperatureThe solution was cooled
  4. washwashed with ice-cold dilute caustic soda
  5. customthe benzene removed in vacuo
  6. additionEthanolic caustic soda (80 g in the minimum amount of ethanol) was added
  7. temperaturethe solution refluxed for 30 minutes
  8. temperaturecooled
  9. additiondiluted with water (one volume)
  10. filtrationThe thick white precipitate was filtered
  11. washwashed with water
  12. customrecrystallized from ethanol

출처 및 근거

ORD 기록
ord-3ba46bbc558341cd85eb6df692fc65f9
출처 데이터셋
uspto-grants-1977_01
특허 번호
US04004018

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