Nitric Acid → HCID 21783433, 화합물

HRID 218270노트

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HRID 218270 반응식
[C:1]([O:4][C:5]1[C:12]([O:13][CH3:14])=[CH:11][CH:10]=[CH:9][C:6]=1[CH:7]=[O:8])(=[O:3])[CH3:2].S(=O)(=O)(O)O.[N+:20]([O-])([OH:22])=[O:21]>>[C:1]([O:4][C:5]1[C:12]([O:13][CH3:14])=[C:11]([N+:20]([O-:22])=[O:21])[CH:10]=[CH:9][C:6]=1[CH:7]=[O:8])(=[O:3])[CH3:2]

참가 물질

4

반응물 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 2517032-Acetoxy-3-methoxybenzaldehyde

생성물 1

HCID 21783433HCID 21783433, 화합물

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온도
-15 °C

실험 절차

42 (42.0 g, 0.22 mol) was added portionwise as a finely ground powder over 1 h to a solution of concentrated sulphuric acid (28 mL) in 100% nitric acid (140 mL) at −20° C. During the addition, the reaction temperature was maintained at around −15° C. The reaction mixture was stirred at −5° C. for a further 40 min, then poured into to ice/water (1 L) and extracted rapidly with toluene (2×). The organic phase was washed successively with 0.25 M NaHCO3 aq. water and brine, dried (Na2SO4) and evaporated to dryness to give crude product (19.8 g) as a yellow oil, which was shown by NMR to contain ˜60% nitro-compounds. Purification of 8 g of this material by column chromatography (three times, SiO2, first eluting with 1:9 EtOAc:cyclohexane, then with 3:7 EtOAc:cyclohexane and finally with 1:1 EtOAc:cyclohexane) gave 43 (2.53 g) in (˜80% purity) together with 2-hydroxy-3-methoxy-4-nitrobenzaldehyde (˜10%). The product was used as such in the next step.

후처리

  1. additionDuring the addition
  2. extractionextracted rapidly with toluene (2×)
  3. washThe organic phase was washed successively with 0.25 M NaHCO3 aq. water and brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated to dryness
  6. customto give crude product (19.8 g) as a yellow oil, which
  7. customPurification of 8 g of this material by column chromatography (three times, SiO2
  8. washfirst eluting with 1:9 EtOAc

출처 및 근거

ORD 기록
ord-dfe6e49bf0174b03ac455a26bf1deeda
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08198302B2

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