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

HRID 504338ノート

反応式

HRID 504338 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 313Hydrochloric Acid溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-7236739dc02b441a995485cfde207d0f
出典データセット
uspto-grants-2010_08
特許番号
US07776874B2

反応ノート

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