Chrysene → 1-Chrysen-6-ylethanone

HRID 1193736

반응식

HRID 1193736 반응식
[CH:1]1[C:18]2[CH:17]=[CH:16][C:15]3[C:6](=[CH:7][CH:8]=[C:9]4[C:14]=3[CH:13]=[CH:12][CH:11]=[CH:10]4)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[Al+3].[Cl-].[Cl-].[Cl-].[CH3:23][C:24](Cl)=[O:25].C1([N+]([O-])=O)C=CC=CC=1>C(Cl)Cl>[C:24]([C:8]1[CH:7]=[C:6]2[C:15](=[C:14]3[C:9]=1[CH:10]=[CH:11][CH:12]=[CH:13]3)[CH:16]=[CH:17][C:18]1[CH:1]=[CH:2][CH:3]=[CH:4][C:5]2=1)(=[O:25])[CH3:23].[C:24]([C:12]1[CH:11]=[CH:10][C:9]2[CH:8]=[CH:7][C:6]3[C:15]([C:14]=2[CH:13]=1)=[CH:16][CH:17]=[C:18]1[C:5]=3[CH:4]=[CH:3][CH:2]=[CH:1]1)(=[O:25])[CH3:23]

참가 물질

5

반응물 2

HCID 9171ChryseneHCID 131715424AlCl3 CH3COCl PhNO2

생성물 2

HCID 1903171-Chrysen-6-ylethanoneHCID 124439383-Acetylchrysene

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Friedel-Crafts reaction of chrysene with AlCl3 /CH3COCl/PhNO2 gave a mixture of 2-, 3-, and 6-acetylchrysenes (285 g, Cambridge Chemical, Inc.). This was stirred and heated in CH2Cl2 (400 mL) and then filtered. The insoluble material, 2-acetylchrysene, was washed copiously with CH2Cl2. The solvent was removed from the filtrate. The resulting solid was dissolved in PhCH3, then the mixture containing the remaining two isomers chromatographed using PhCH3 as eluting solvent on a plug of SiO2 (1 kg). The faster eluting isomer is 6-acetylchrysene while the slower is 3-acetylchrysene. The chromatography gave 132 g of impure 6-acetylchrysene, and 76 g of impure 3-acetylchrysene. These materials were used without further purification. Pure samples of the compounds were obtained by preparative HPLC using PhCH3 as the eluting solvent.

후처리

  1. customgave
  2. filtrationfiltered
  3. washThe insoluble material, 2-acetylchrysene, was washed copiously with CH2Cl2
  4. customThe solvent was removed from the filtrate
  5. dissolutionThe resulting solid was dissolved in PhCH3
  6. additionthe mixture containing the remaining two isomers
  7. customchromatographed
  8. washas eluting solvent on a plug of SiO2 (1 kg)
  9. washThe faster eluting isomer

출처 및 근거

ORD 기록
ord-7c4126f6cef14df9a4386784a0f1d3fb
출처 데이터셋
uspto-grants-1989_03
특허 번호
US04810727

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