Methanol → Methyl 2-methyl-5-nitrobenzoate

HRID 8954

반응식

HRID 8954 반응식
[CH3:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].OS(O)(=O)=O.[CH3:19]O>>[CH3:19][O:5][C:4](=[O:6])[C:3]1[CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=[CH:10][C:2]=1[CH3:1]

참가 물질

4

반응물 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 5196832-Methyl-5-nitrobenzoic acid

생성물 1

HCID 4377758Methyl 2-methyl-5-nitrobenzoate수율 73%

실험 절차

A solution of 2-methyl-5-nitrobenzoic acid (1.91 g, 10.6 mmol) and H2SO4 (catalytic) in MeOH (25 mL) was heated at reflux for 16 h, then concentrated in vacuo. The residue was dissolved in CH2Cl2 (50 mL), washed with saturated NaHCO3(aq) (2×40 mL), then dried (MgSO4), filtered, and concentrated in vacuo to give yellow crystals (1.50 g, 73%). 1H NMR (CDCl3) δ 2.72 (s, 3H), 3.96 (s, 3H), 7.44 (d, 1H, J=9.0 Hz), 8.24 (dd, 1H, J=9.0, 3.0 Hz), 8.78 (d, 1H, J=3.0 Hz).

후처리

  1. temperatureat reflux for 16 h
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in CH2Cl2 (50 mL)
  4. washwashed with saturated NaHCO3(aq) (2×40 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-7b31324e4f2c4d8182cec42303622a5d
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091217B2

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