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

HRID 38637

Reaction equation

HRID 38637 reaction equation
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]

Participants

5

Reactant 3

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

Product 1

HCID 2555821-(5-Chloro-2-nitrophenyl)ethanoneYield 55.8%

Reagents, catalysts & solvents 1

HCID 944Nitric AcidSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-fb4d35d4eb8d41f68fff833a02e62f18
Source dataset
uspto-grants-2013_09
Patent number
US08524740B2

Linked notes

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