Carbon Dioxide → 9H-Thioxanthene-9-carboxylic acid

HRID 581648

반응식

HRID 581648 반응식
[CH:1]1[C:14]2[CH2:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[S:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[Li]CCCC.[C:20](=[O:22])=[O:21]>C1COCC1>[CH:1]1[C:14]2[CH:13]([C:20]([OH:22])=[O:21])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[S:6][C:5]=2[CH:4]=[CH:3][CH:2]=1

참가 물질

5

반응물 3

HCID 280Carbon DioxideHCID 67495ThioxantheneHCID 178418339Butyllithium

생성물 1

HCID 125156549H-Thioxanthene-9-carboxylic acid

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Thioxanthene, 9.1 g, was dissolved in 100 mL of dry THF. The solution was cooled in an ice bath and n-BuLi (24 mL of 2.5M solution) was added dropwise. The red solution was stirred at room temperature for one hour. Powdered CO2 was added (ca. 150 g) causing formation of a white precipitate. After stirring an additional hour the mixture was evaporated and the residue dissolved in water. The aqueous solution was extracted with CH2Cl2, and neutralized with HCl. The precipitated product was dissolved in ether, dried and evaporated producing thioxanthene-9-carboxylic acid as a white solid (8.8 g): 1H NMR (DMSO-d6) δ 5.25 (s, 1H), 7.30 (m, 4H), 7.49 (m, 4H), 12.60 (s, 1H).

후처리

  1. temperatureThe solution was cooled in an ice bath
  2. stirringAfter stirring an additional hour the mixture
  3. customwas evaporated
  4. dissolutionthe residue dissolved in water
  5. extractionThe aqueous solution was extracted with CH2Cl2
  6. dissolutionThe precipitated product was dissolved in ether
  7. customdried
  8. customevaporated

출처 및 근거

ORD 기록
ord-bf628bdd78d341a59b8a4d25a45ea027
출처 데이터셋
uspto-grants-1999_07
특허 번호
US05922558

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