Carbon Disulfide → Methyl1-[4-(chloroacetyl)phenyl]cyclopropanecarboxylate

HRID 504338노트

반응식

HRID 504338 반응식
[Cl-].[Cl-].[Cl-].[Al+3].[C:5]1([C:11]2([C:14]([O:16][CH3:17])=[O:15])[CH2:13][CH2:12]2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[Cl:18][CH2:19][C:20](Cl)=[O:21].C(=S)=S>Cl>[Cl:18][CH2:19][C:20]([C:8]1[CH:9]=[CH:10][C:5]([C:11]2([C:14]([O:16][CH3:17])=[O:15])[CH2:13][CH2:12]2)=[CH:6][CH:7]=1)=[O:21]

참가 물질

6

반응물 4

HCID 6348Carbon DisulfideHCID 6577Chloroacetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 12861006Methyl 1-phenylcyclopropane-1-carboxylate

생성물 1

HCID 86602275Methyl1-[4-(chloroacetyl)phenyl]cyclopropanecarboxylate

시약·촉매·용매 1

HCID 313Hydrochloric Acid용매

실험 절차

Aluminum trichloride (7.9 g, 0.060 mol) was added in portions to a mixture of methyl 1-phenylcyclopropanecarboxylate (3.5 g, 0.020 mol) and chloroacetyl chloride (2.0 mL, 0.026 mol) in carbon disulfide (40 mL, 0.7 mol) at 15-25° C. and then the reaction mixture was stirred at room temperature for 2 hours. The mixture was poured into conc. HCl (10 mL) in ice (100 g) and then extracted with ether. The ether extract was washed with brine, dried and concentrated. The product was purified by CombiFlash using hexane/EtOAc (max.EA 20%). The final product was analyzed by 1H NMR, which showed that the product was a mixture of para and meta substituted isomers with a ratio of 3:2.

후처리

  1. extractionextracted with ether
  2. extractionThe ether extract
  3. washwas washed with brine
  4. customdried
  5. concentrationconcentrated
  6. customThe product was purified by CombiFlash
  7. additiona mixture of para and meta

출처 및 근거

ORD 기록
ord-7236739dc02b441a995485cfde207d0f
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07776874B2

반응 노트

불러오는 중…