Nitric Acid → 2,5-Dichloro-3-nitrobenzoic acid

HRID 885731

反応式

HRID 885731 の反応式
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[N+:12]([O-])([OH:14])=[O:13]>OS(O)(=O)=O>[Cl:1][C:2]1[C:10]([N+:12]([O-:14])=[O:13])=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

参加物

4

反応物 2

HCID 944Nitric AcidHCID 57842,5-Dichlorobenzoic acid

生成物 1

HCID 69512,5-Dichloro-3-nitrobenzoic acid収率 95.5%

試薬・触媒・溶媒 1

HCID 1118Sulfuric Acid溶媒

反応条件

温度
0 °C

実験手順

To a solution of 2,5-dichlorobenzoic acid (3 g, 15.7 mmol) in H2SO4 (16 mL) at 0° C. was added dropwise fuming nitric acid (1.4 mL, 31.4 mmol) and the reaction mixture was stirred for 5 minutes at 0° C., and was then gradually allowed to warm to over 20 minutes. The reaction was treated with ice water and extracted with EtOAc. The organic layer was washed with water and brine then dried (Na2SO4), filtered and concentrated to afford 3.54 g (48%) of 2,5-dichloro-3-nitrobenzoic acid which is contaminated with 3,6-dichloro-2-nitrobenzoic acid (40%): 1H NMR (300 MHz, CD3OD) δ 7.73 (s, 1H) 8.06 (d, J=2.6 Hz, 1H) 8.11 (d, J=2.6 Hz, 1H).

後処理

  1. temperatureto warm to over 20 minutes
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with water and brine
  4. dry with materialthen dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-f573a1291a0c42a68bef85d7252c04fa
出典データセット
uspto-grants-2012_08
特許番号
US08242260B2

関連ノート

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