Methanol → Methyl 3-hydroxy-2-nitrobenzoate

HRID 415162

반응식

HRID 415162 반응식
[OH:1][C:2]1[C:3]([N+:11]([O-:13])=[O:12])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].OS(O)(=O)=O.[CH3:19]O>>[OH:1][C:2]1[C:3]([N+:11]([O-:13])=[O:12])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([O:7][CH3:19])=[O:6]

참가 물질

4

반응물 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 2932913-Hydroxy-2-nitrobenzoic acid

생성물 1

HCID 13659833Methyl 3-hydroxy-2-nitrobenzoate

실험 절차

A solution of 3-hydroxy-2-nitrobenzoic acid (51 g) and con.H2SO4 (5 mL) in anhydrous methanol (450 mL) was heated to reflux for 48 hr. The mixture was concentrated to remove methanol, and the residue was partitioned between water (500 mL) and ethyl acetate (800 mL). The organic layer was washed with brine (300 mL), dried over anhydrous sodium sulfate, and concentrated to give crude compound. The crude product was purified by chromatography (silica gel, petroleum ether/ethyl acetate=40:1 to 5:1) to give methyl 3-hydroxy-2-nitrobenzoate (28 g) 1H-NMR (400 MHz, CDCl3) δ 3.8 (s, 3H), 7.32-7.34 (d, J=8.4 Hz, 1H), 7.39-7.41 (d, J=8.0 Hz, 1H), 7.48-7.52 (t, J=8.0 Hz, 1H), 11.37 (s, 1H); LC-MS (m/z) 198 [M+1]+.

후처리

  1. temperatureto reflux for 48 hr
  2. concentrationThe mixture was concentrated
  3. customto remove methanol
  4. customthe residue was partitioned between water (500 mL) and ethyl acetate (800 mL)
  5. washThe organic layer was washed with brine (300 mL)
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. customto give crude compound
  9. customThe crude product was purified by chromatography (silica gel, petroleum ether/ethyl acetate=40:1 to 5:1)

출처 및 근거

ORD 기록
ord-898faeee71a3496982246edc800080a2
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08088760B2

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