Sulfuric Acid → 1-(5-Chloro-2-nitrophenyl)ethanone

HRID 38637

反応式

HRID 38637 の反応式
OS(O)(=O)=O.[N+:6]([O-:9])(O)=[O:7].OS(O)(=O)=O.[CH3:15][C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=1)=[O:17]>[N+]([O-])(O)=O>[CH3:15][C:16]([C:18]1[CH:19]=[C:20]([Cl:24])[CH:21]=[CH:22][C:23]=1[N+:6]([O-:9])=[O:7])=[O:17]

参加物

5

反応物 3

HCID 1118Sulfuric AcidHCID 149331-(3-Chlorophenyl)ethanoneHCID 71777668Sulfuric acid, mixt. with nitric acid

生成物 1

HCID 2555821-(5-Chloro-2-nitrophenyl)ethanone収率 55.8%

試薬・触媒・溶媒 1

HCID 944Nitric Acid溶媒

実験手順

65% HNO3 (80 ml) was stirred at −5° C.±1° C. and 98% H2SO4 (10 mix 10) was added dropwise. To the stirring solution of HNO3/H2SO4 was added 3-chloroacetophenone (54) (12.0 g, 77.6 mmol). The mixture was stirred at −5□±1□ for 3 h and poured into crushed ice, and extracted with CH2Cl2. The extract was dried over MgSO4 and evaporated. The crude product was purified by column chromatography (silica gel, n-hexane/EtOAc=15:1) to give 55 as yellow solid (9.3 g, 46.6 mmol). Yield: 55.8%; mp 47-49° C.; 1H-NMR (CDCl3, 200 MHz): δ 2.48 (s, 3H), 7.32 (d, J=2.4 Hz, 1H), 7.49 (dd, J=8.8, 2.2 Hz, 1H), 8.00 (d, J=8.8 Hz, 1H); 13C-NMR (CDCl3, 50 MHz) δ: 198.27, 143.78, 141.05, 139.44, 130.55, 127.36, 125.91, 30.06; Anal. Calcd for C8H6ClNO3: C, 48.14; H, 3.03; N, 7.02.

後処理

  1. additionpoured
  2. custominto crushed ice
  3. extractionextracted with CH2Cl2
  4. dry with materialThe extract was dried over MgSO4
  5. customevaporated
  6. customThe crude product was purified by column chromatography (silica gel, n-hexane/EtOAc=15:1)

出典と根拠

ORDレコード
ord-fb4d35d4eb8d41f68fff833a02e62f18
出典データセット
uspto-grants-2013_09
特許番号
US08524740B2

関連ノート

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