Nitric Acid → 1-Chloro-5-methoxy-2-methyl-4-nitrobenzene

HRID 272680ノート

反応式

HRID 272680 の反応式
C(OC(=O)C)(=O)C.[N+:8]([O-:11])(O)=[O:9].[Cl:12][C:13]1[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][C:14]=1[CH3:21]>O>[Cl:12][C:13]1[CH:18]=[C:17]([O:19][CH3:20])[C:16]([N+:8]([O-:11])=[O:9])=[CH:15][C:14]=1[CH3:21]

参加物

5

反応物 3

HCID 944Nitric AcidHCID 7918Acetic AnhydrideHCID 69517572-Chloro-4-methoxytoluene

生成物 1

HCID 138601931-Chloro-5-methoxy-2-methyl-4-nitrobenzene収率 71%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
-5 °C

実験手順

Acetic anhydride (10 mL) at −10° C. was treated with concentrated nitric acid (>69% pure, 1 mL) and then treated portionwise with 2-chloro-4-methoxy-1-methylbenzene (0.78 g, 5 mmol) at a rate that maintained the internal temperature lower than −5° C. The solution was stirred for additional one hour while warming to room temperature, poured into an ice and water mixture, and extracted with ethyl acetate several times. The organic layers were combined, washed with 10% Na2CO3 and brine, dried (MgSO4), and concentrated under vacuum. The residue was purified by flash column chromatography on silica gel eluting with 9:1 hexanes/ethyl acetate to provide 0.75 g (71%) of the desired product. MS (DCI) m/e 219 (M+NH4)+; 1H NMR (CDCl3, 300 MHz) δ 7.78 (s, 1H), 7.09 (s, 1H), 3.94 (s, 3H), 2.35 (s, 3H).

後処理

  1. temperaturewhile warming to room temperature
  2. extractionextracted with ethyl acetate several times
  3. washwashed with 10% Na2CO3 and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by flash column chromatography on silica gel eluting with 9:1 hexanes/ethyl acetate

出典と根拠

ORDレコード
ord-1aa7025d750e4edb970f742dc689a65a
出典データセット
uspto-grants-2008_11
特許番号
US07456169B2

反応ノート

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