Sodium Dithionite → Anthracene-1,4-diol

HRID 2306897

반응식

HRID 2306897 반응식
[C:1]1(=[O:16])[C:14]2[C:5](=[CH:6][C:7]3[C:12]([CH:13]=2)=[CH:11][CH:10]=[CH:9][CH:8]=3)[C:4](=[O:15])[CH:3]=[CH:2]1.S(S([O-])=O)([O-])=O.[Na+].[Na+]>O.O1CCOCC1.C(Cl)(Cl)Cl.CS(C)=O.CN(C=O)C>[OH:15][C:4]1[C:5]2[C:14](=[CH:13][C:12]3[C:7]([CH:6]=2)=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:1]([OH:16])=[CH:2][CH:3]=1

참가 물질

8

반응물 2

HCID 24489Sodium DithioniteHCID 694571,4-Anthraquinone

생성물 1

HCID 12631814Anthracene-1,4-diol수율 87%

시약·촉매·용매 5

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매2회HCID 6212Chloroform용매HCID 6228Dimethylformamide용매HCID 312751,4-Dioxane용매

실험 절차

To a 250 ml-round-bottom flask, was added 2 g (MW 208; 0.0096 mol) of 1,4-anthracenedione (4). To it a solution of 6.6816 g (MW 174; 0.0384 mol) of sodium hydrosulfite in 50 mL of distilled water and 50 mL of 1,4-dioxane were added. The resulting mixture was stirred at room temperature for 2-3 hours. The reaction progress is checked with TLC (using CH2Cl2:hexanes:ether 1:1:0.2 as the eluant). The mixture was transferred to a 500-mL beaker slowly, cooled over an ice-water bath, and added 100 mL of distilled water. Dark green solids precipitated. The beaker was covered with aluminum foil, and placed in the refrigerator for 1 h. The solid was filtered through a glass fritted funnel and the product was washed with 30 mL of distilled water twice. The solid product was dried under vacuum to give 1.754 g (87% yield), mp 167-169° C.; 1H NMR (CDCl3 contains a small amount of p-dioxane) d 8.7 (m, 2H, C 9,10 Hs), 8.05 (m, 2H, C 5,8 Hs), 7.5 (s, 2H, C 6,7 Hs), 6.6 (s, 2H, C 2,3 Hs). The diol is insoluble in chloroform but soluble in DMSO and DMF.

후처리

  1. temperaturecooled over an ice-water bath
  2. customDark green solids precipitated
  3. waitplaced in the refrigerator for 1 h
  4. filtrationThe solid was filtered through a glass fritted funnel
  5. washthe product was washed with 30 mL of distilled water twice
  6. customThe solid product was dried under vacuum
  7. customto give 1.754 g (87% yield), mp 167-169° C.

출처 및 근거

ORD 기록
ord-505dc663300d46fb9f58a636cb9755a4
출처 데이터셋
uspto-grants-2004_12
특허 번호
US06828450B2

연결된 노트

불러오는 중…