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

HRID 272680노트

반응식

HRID 272680 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

HCID 138601931-Chloro-5-methoxy-2-methyl-4-nitrobenzene수율 71%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
-5 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-1aa7025d750e4edb970f742dc689a65a
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07456169B2

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